chemistry

Nature's Herbarium Pharmacopeia: Strange Psychedelic Plants

Alex Coppen

• 32 min read
Nature's Herbarium Pharmacopeia: Strange Psychedelic Plants

Mother Nature's pantry is bursting with electrochemical wonder. Thousands of psychedelic plants have been catalogued by chemists and botanists. As miniature laboratories, they produce molecules of such staggering complexity, its often hard to believe your eyes.

It can be hard to find a reference source or encyclopaedia index where you can start on your exploration if you are a chemist. But you soon discover why a large degree of scientists are fascinated by the planet's natural medicine cabinet.

Microscopic Artistry Few Ever See

There are days when you look at the structure of molecules and think God is showing off. Until you realise nobody ever really gets to see them. There is a mathematical beauty in the chemical world which is simply breathtaking.

The compound Ibogaine, found in the root bark of Tabernanthe iboga is a substituted tryptamine with the reported ability to break addiction to opiates and opoids. Its structure is wondrous.

(1R,15R,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene

Cocaine, a benzoate ester tropane alkaloid from Erythroxylum coca is where all our dental anaesthetics are derived from. Few have ever tried to reproduce it in a laboratory because of its sophisticated structure.

methyl (1R,2R,3S,5S)-3- (benzoyloxy)-8-methyl-8-azabicyclo[3.2.1] octane-2-carboxylate

Why Do They Exist At All?

The greatest mystery is why, perhaps, there are plants which have psychedelic effects on us. Why do we have receptors for them to bind to?

Much can be traced back to the shared evolutionary history of plants and animals, as well as the similarities in the basic biochemistry of living organisms. Many of the receptors and neurotransmitter systems in the human brain have evolved from ancient molecular pathways that are present in simpler organisms, including plants. As a result, some compounds produced by plants can interact with these receptors due to their structural similarity to endogenous neurotransmitters or signaling molecules.

Plants and animals have co-evolved over millions of years, and some plants may have developed compounds that interact with animal neurotransmitter systems as a defense mechanism against herbivory or to encourage the dispersal of their seeds by animals. In turn, animals have evolved receptors that respond to these compounds.

Some plant compounds are structurally similar to endogenous neurotransmitters or signaling molecules in the human brain (i.e. ones we naturally produce in our bodies already). These compounds can bind to and activate or inhibit the same receptors that respond to the endogenous molecules, resulting in psychoactive effects. For example, the psychoactive compound in marijuana, THC, binds to the brain's endocannabinoid receptors (CB1 and CB2), which normally respond to naturally occurring cannabinoids in the body.

Some plant compounds may not directly bind to receptors in the brain but instead modulate (i.e. make stronger or weaker) the activity of endogenous neurotransmitter systems. For example, some compounds may inhibit the breakdown or reuptake of neurotransmitters, leading to increased levels of these molecules in the brain and altered neural activity.

Grouping The Pantry's Shelves

Psychoactive compounds can broadly be categorised into ten different groups, based on their molecular structure. Often these are used as "backbone" templates for new molecules.

The Ephedra genus, for example, found all over the world, produces the phenethylamine alkaloid Ephedrine ((1R,2S)-2-(methylamino)-1-phenylpropan-1-ol). When reduced, the result is 4-methyl-amphetamine; when oxidated, the result is methcathinone. If we continue to methylate the latter, the result is Mephedrone (4-methyl-methcathinone). As such, Ephedrine is the natural template for amphetamines.

  1. Tryptamines: derived from tryptamine, often with psychedelic effects (e.g., DMT, Psilocybin, Psilocin, 5-MeO-DMT, Bufotenin)
  2. Phenethylamines: a phenethylamine core structure, including stimulants and psychedelics (e.g., Mescaline, MDMA, Amphetamine, Cathinone)
  3. Benzofurans: a benzofuran ring, often with entactogenic effects (e.g., 5-APB, 6-APB, 5-MAPB)
  4. Lysergamides: derived from lysergic acid, known for their potent psychedelic effects (e.g., LSD, LSA, ETH-LAD)
  5. Beta-carbolines: a beta-carboline structure, often with MAO-inhibiting and mild psychedelic effects (e.g., Harmine, Harmaline, Tetrahydroharmine)
  6. Piperazines: a piperazine ring, often with stimulant or entactogenic effects (e.g., BZP, mCPP, TFMPP)
  7. Cannabinoids: found in cannabis or synthetic analogues, known for their varied effects (e.g., THC, CBD, CBN, JWH-018)
  8. Opioids: act on opioid receptors, known for their pain-relieving and euphoric effects (e.g., Morphine, Codeine, Thebaine, Kratom alkaloids)
  9. Dissociatives: causing dissociative effects, often acting as NMDA receptor antagonists (e.g., Ketamine, PCP, DXM, Salvinorin A)
  10. Xanthines: a xanthine core structure, known for their stimulant effects (e.g., Caffeine, Theobromine, Theophylline)

Strange Effects In Humans

Although most plants produce many different compounds simultaneously, we can also broadly group their activity by their strongest and most pronounced effects. Cannabis sativa, for example, contains over 100 cannabinoids; only three are used recreationally. Two cannabinoids are found naturally in the human body ("endo"): anandamide, or AEA, and 2-arachidonoyl glycerol, known as 2-AG.

Hallucinogens/Psychedelics

Many psychedelic compounds, such as psilocybin, DMT, and mescaline, bind to and activate serotonin receptors, particularly the 5-HT2A receptor subtype. Activation of these receptors leads to increased excitatory neurotransmission and altered perception, mood, and cognition. Some psychedelics, like ibogaine, may also interact with other neurotransmitter systems, such as the dopaminergic and glutamatergic systems.

  • Cannabis (THC)
  • Psilocybin Mushrooms (Psilocybin, Psilocin)
  • Peyote (Mescaline)
  • Ayahuasca (DMT, Harmine, Harmaline)
  • Salvia (Salvinorin A)
  • Morning Glory (Ergine)
  • Hawaiian Baby Woodrose (Ergine)
  • Iboga (Ibogaine)
  • Yopo (Bufotenin, DMT)
  • Acacia (DMT, Mescaline)
  • Chacruna (DMT)
  • Chaliponga (DMT, 5-MeO-DMT)

Stimulants

Stimulant compounds typically interact with the dopamine and norepinephrine neurotransmitter systems. Compounds like cocaine and cathinone inhibit the reuptake of dopamine and norepinephrine, leading to increased levels of these neurotransmitters in the synaptic cleft and enhanced neurotransmission. Other stimulants, such as caffeine, act as adenosine receptor antagonists, promoting wakefulness and alertness.

  • Tobacco (Nicotine)
  • Coca (Cocaine)
  • Khat (Cathinone, Cathine)
  • Ephedra (Ephedrine, Pseudoephedrine)
  • Guarana (Caffeine)
  • Yohimbe (Yohimbine)
  • Betel Nut (Arecoline)
  • Guayusa (Caffeine, Theobromine)
  • Cacao (Theobromine, Caffeine)

Sedatives/Depressants

Sedative compounds often interact with the gamma-aminobutyric acid (GABA) neurotransmitter system, which is the primary inhibitory neurotransmitter in the brain. Compounds like kavalactones and valerenic acid may enhance the effects of GABA by binding to GABA receptors or modulating the activity of GABA-producing enzymes, leading to increased inhibitory neurotransmission and feelings of relaxation and sedation. Opioid compounds, such as morphine and codeine, bind to opioid receptors in the brain, leading to reduced pain perception and feelings of euphoria.

  • Opium Poppy (Morphine, Codeine)
  • Kratom (Mitragynine, 7-Hydroxymitragynine)
  • Kava (Kavalactones)
  • Valerian (Valerenic acid, Isovaleric acid)
  • Passionflower (Harman alkaloids)
  • Catnip (Nepetalactone)
  • Hops (Humulone, Lupulone)

Anxiolytics

Anxiolytic compounds typically interact with the GABA neurotransmitter system, similar to sedatives. These compounds may enhance the effects of GABA, leading to reduced anxiety and increased relaxation. Some anxiolytic compounds, like baicalin and baicalein, may also interact with serotonin receptors, modulating serotonergic neurotransmission.

  • Kava (Kavalactones)
  • Passionflower (Harman alkaloids)
  • Ashwagandha (Withanolides)
  • Lemon Balm (Rosmarinic acid, Linalool)
  • Skullcap (Baicalin, Baicalein)

Antidepressants

Antidepressant compounds often interact with the serotonin, norepinephrine, and dopamine neurotransmitter systems. Compounds like hypericin and hyperforin (found in St. John's Wort) may inhibit the reuptake of these neurotransmitters, leading to increased levels in the synaptic cleft and enhanced neurotransmission. Other compounds, such as 5-HTP (found in Griffonia), serve as precursors to serotonin, increasing its production in the brain.

  • St. John's Wort (Hypericin, Hyperforin)
  • Saffron (Crocin, Safranal)
  • Griffonia (5-HTP)

Cognitive Enhancers/Nootropics

Cognitive enhancers and nootropics can have diverse mechanisms of action, targeting various neurotransmitter systems and brain pathways. Some compounds, like ginkgolides and bilobalide (found in Ginkgo biloba), may improve cerebral blood flow and protect against oxidative stress, supporting cognitive function. Others, such as bacosides (found in Bacopa monnieri), may modulate cholinergic and serotonergic neurotransmission, enhancing memory and learning.

  • Ginkgo (Ginkgolides, Bilobalide)
  • Bacopa monnieri (Bacoside A, Bacoside B)
  • Gotu Kola (Asiaticoside, Madecassoside)
  • Ashwagandha (Withanolides)
  • Rhodiola rosea (Salidroside, Rosavin)
  • Lion's Mane Mushroom (Hericenones, Erinacines)

Adaptogens

Adaptogens are believed to help the body adapt to stress by modulating the hypothalamic-pituitary-adrenal (HPA) axis and other stress-response systems. Compounds like withanolides (found in Ashwagandha) and salidroside (found in Rhodiola rosea) may interact with the HPA axis, reducing cortisol levels and promoting a balanced stress response. Adaptogens may also have neuroprotective and anti-inflammatory effects, supporting overall brain health and resilience.

  • Ashwagandha (Withanolides)
  • Rhodiola rosea (Salidroside, Rosavin)
  • Ginseng (Ginsenosides)
  • Holy Basil (Eugenol, Ursolic acid)
  • Eleuthero (Eleutherosides)

The List: The Planet's Strangest Plants

One day, someone is going to produce a proper reference library on these wondrous photochemical laboratories we can all have on our bookshelf. However, until then...

  1. Cannabis (Cannabis sativa) Cannabis, also known as marijuana, is a widely cultivated plant containing the psychoactive compounds THC (Δ9-tetrahydrocannabinol) and CBD (Cannabidiol). THC is found in concentrations ranging from 0.1-30% and is responsible for the plant's euphoric, relaxing, and perception-altering effects. CBD, present in concentrations of 0.1-25%, is known for its potential medicinal properties, such as pain relief, anxiety reduction, and anti-epileptic effects.
  2. Tobacco (Nicotiana tabacum) Tobacco is a widely cultivated plant containing the psychoactive compound nicotine, found in concentrations ranging from 0.6-3%. Nicotine is known for its stimulating and relaxing effects, as well as its highly addictive properties. Tobacco has been used for centuries for recreational purposes and has limited medical applications in smoking cessation through nicotine replacement therapy.
  3. Coca (Erythroxylum coca) Coca is a plant native to South America, containing the psychoactive compound cocaine, found in concentrations ranging from 0.1-0.9%. Cocaine is known for its euphoric, energy-increasing, and local anesthetic effects. While coca leaves have been traditionally used by indigenous South American cultures, cocaine has limited medical applications as a local anesthetic.
  4. Opium Poppy (Papaver somniferum) Opium poppy is a plant cultivated worldwide, containing several psychoactive compounds, including morphine (4-21%), codeine (0.7-2.5%), and thebaine (0.1-2.5%). These compounds are known for their pain-relieving, euphoric, and sedative effects, as well as their potential for respiratory depression. Medically, opioids derived from opium poppy are used for pain management, cough suppression, and diarrhea treatment.
  5. Psilocybin Mushrooms (Psilocybe spp.) Psilocybin mushrooms are fungi containing the psychoactive compounds psilocybin (0.2-1%) and psilocin (0.1-0.8%). These compounds are known for their ability to alter perception, induce euphoria, and promote introspection. Psilocybin has been the subject of research for its potential therapeutic applications in the treatment of depression, anxiety, and addiction.
  6. Peyote (Lophophora williamsii) Peyote is a small cactus native to Mexico and the southwestern United States, containing the psychoactive compound mescaline (0.4-5%). Mescaline is known for its ability to alter perception, induce introspection, and produce euphoria. Peyote has been traditionally used in Native American ceremonies and has limited medical applications.
  7. Ayahuasca (Banisteriopsis caapi & Psychotria viridis) Ayahuasca is a brew made from the combination of Banisteriopsis caapi and Psychotria viridis, containing the psychoactive compounds DMT (0.1-0.66%), harmine (0.05-1.7%), and harmaline (0.05-1.7%). This combination is known for producing intense visual hallucinations, introspection, and spiritual experiences. Ayahuasca has been traditionally used in South American shamanic practices and has been the subject of research for its potential therapeutic applications in the treatment of depression and addiction.
  8. Salvia (Salvia divinorum) Salvia is a plant native to Mexico, containing the psychoactive compound salvinorin A (0.1-4%). Salvinorin A is known for its ability to induce intense hallucinations, dissociation, and altered perception. Salvia has been traditionally used by the Mazatec people and has been the subject of research for its potential applications in the treatment of addiction and pain.
  9. Kratom (Mitragyna speciosa) Kratom is a tree native to Southeast Asia, containing the psychoactive compounds mitragynine (0.5-1.5%) and 7-hydroxymitragynine (0.01-0.04%). These compounds are known for their pain-relieving, euphoric, and stimulating effects at low doses, and sedative effects at high doses. Kratom has been traditionally used in Southeast Asia and has been the subject of limited research for its potential applications in the treatment of pain, anxiety, and opioid withdrawal.
  10. Khat (Catha edulis) Khat is a shrub native to East Africa and the Arabian Peninsula, containing the psychoactive compounds cathinone (0.1-0.6%) and cathine (0.05-0.3%). These compounds are known for their stimulating effects, inducing euphoria, increased alertness, and appetite suppression. Khat has been traditionally used in East Africa and the Middle East for social and cultural purposes.
  11. Kava (Piper methysticum) Kava is a plant native to the Pacific Islands, containing psychoactive compounds known as kavalactones (3-20%), including kavain, methysticin, and yangonin. These compounds are known for their relaxing, anxiolytic, and mildly euphoric effects. Kava has been traditionally used in Pacific Island cultures and has been the subject of limited research for its potential applications in the treatment of anxiety and stress.
  12. Betel Nut (Areca catechu) Betel nut is the seed of the Areca catechu palm, native to Asia and the Pacific Islands, containing the psychoactive compound arecoline (0.1-0.7%). Arecoline is known for its stimulating effects, inducing mild euphoria, increased alertness, and salivation. Betel nut has been traditionally used in Asia and the Pacific Islands for social and cultural purposes.
  13. Morning Glory (Ipomoea spp.) Morning glory is a flowering plant containing the psychoactive compounds ergine (LSA) (0.01-0.06%) and isoergine (0.001-0.005%). These compounds are known for their mild psychedelic effects, sedation, and nausea. Morning glory has been traditionally used by Aztecs and other indigenous groups for spiritual and ritualistic purposes.
  14. Hawaiian Baby Woodrose (Argyreia nervosa) Hawaiian baby woodrose is a perennial climbing vine native to India and Hawaii, containing the psychoactive compound ergine (LSA) (0.1-0.4%). Ergine is known for its mild psychedelic effects, sedation, and nausea. Hawaiian baby woodrose has been traditionally used in Ayurvedic medicine for various purposes.
  15. Ephedra (Ephedra sinica) Ephedra is a shrub native to Asia and North America, containing the psychoactive compounds ephedrine (0.5-2%) and pseudoephedrine (0.1-0.5%). These compounds are known for their stimulating effects, increasing energy and suppressing appetite. Ephedra has been used in traditional Chinese medicine and has limited medical applications as a decongestant and bronchodilator.
  16. Guarana (Paullinia cupana) Guarana is a climbing plant native to the Amazon basin, containing the psychoactive compound caffeine (2-7%). Caffeine is known for its stimulating effects, increasing alertness and improving cognitive performance. Guarana has been traditionally used by indigenous Amazonian tribes and has limited medical applications for fatigue and weight loss.
  17. Yohimbe (Pausinystalia johimbe) Yohimbe is a tree native to West Africa, containing the psychoactive compound yohimbine (0.5-6%). Yohimbine is known for its stimulating effects, increasing blood flow and inducing anxiety. Yohimbe has been traditionally used in West African medicine and has limited medical applications for erectile dysfunction and weight loss.
  18. Ashwagandha (Withania somnifera) Ashwagandha is a small shrub native to India and Nepal, containing psychoactive compounds known as withanolides, including withaferin A and withanolide A (0.1-0.5%). These compounds are known for their stress-reducing, anxiolytic, and cognitive-enhancing effects. Ashwagandha has been traditionally used in Ayurvedic medicine and has been the subject of research for its potential applications in the treatment of stress, anxiety, and cognitive disorders.
  19. Ginkgo (Ginkgo biloba) Ginkgo is a tree native to China, containing psychoactive compounds known as ginkgolides (0.06-0.2%) and bilobalide (0.13-0.5%). These compounds are known for their cognitive-enhancing effects and ability to improve blood circulation. Ginkgo has been used in traditional Chinese medicine and has been the subject of research for its potential applications in the treatment of dementia, Alzheimer's disease, and tinnitus.
  20. Valerian (Valeriana officinalis) Valerian is a perennial flowering plant native to Europe and Asia, containing psychoactive compounds valerenic acid (0.1-0.8%) and isovaleric acid (0.2-1%). These compounds are known for their sedative, anxiolytic, and sleep-enhancing effects. Valerian has been traditionally used in European herbal medicine and has been the subject of research for its potential applications in the treatment of insomnia and anxiety.
  21. Passionflower (Passiflora incarnata) Passionflower is a perennial climbing vine native to North and South America, containing psychoactive compounds known as harman alkaloids, including harmine and harmaline (0.1-0.5%). These compounds are known for their sedative, anxiolytic, and mild psychoactive effects. Passionflower has been traditionally used in American herbal medicine and has been the subject of research for its potential applications in the treatment of anxiety and insomnia.
  22. St. John's Wort (Hypericum perforatum) St. John's Wort is a perennial flowering plant native to Europe and Asia, containing psychoactive compounds hypericin (0.1-0.3%) and hyperforin (2-4%). These compounds are known for their antidepressant and anxiolytic effects. St. John's Wort has been traditionally used in European herbal medicine and has been the subject of extensive research for its potential applications in the treatment of depression and anxiety.
  23. Damiana (Turnera diffusa) Damiana is a shrub native to Mexico, Central America, and South America, containing psychoactive compounds damianin (0.2-0.7%) and gonzalitosin I (0.1-0.3%). These compounds are known for their mild euphoric, relaxing, and aphrodisiac effects. Damiana has been traditionally used in Mexican herbal medicine for sexual health and anxiety.
  24. Catnip (Nepeta cataria) Catnip is a perennial herb native to Europe and Asia, containing the psychoactive compound nepetalactone (0.2-1%). Nepetalactone is known for its sedative and anxiolytic effects in humans, and its stimulating effects in cats. Catnip has been traditionally used in European herbal medicine for anxiety and insomnia.
  25. Muira Puama (Ptychopetalum olacoides) Muira Puama is a small tree native to the Amazon rainforest, containing psychoactive compounds muirapuamine (0.1-0.5%) and muirapuamine A (0.05-0.3%). These compounds are known for their mild stimulating, aphrodisiac, and cognitive-enhancing effects. Muira Puama has been traditionally used in Brazilian herbal medicine for sexual health and cognitive enhancement.
  26. Sinicuichi (Heimia salicifolia) Sinicuichi is a shrub native to Mexico and Central America, containing psychoactive compounds cryogenine (0.1-0.5%) and vertine (0.05-0.3%). These compounds are known for their mild psychedelic effects and auditory distortions. Sinicuichi has been traditionally used by indigenous groups in Mexico for spiritual and ritualistic purposes.
  27. Blue Lotus (Nymphaea caerulea) Blue lotus is a water lily native to Egypt and East Africa, containing psychoactive compounds apomorphine (0.001-0.005%) and nuciferine (0.05-0.2%). These compounds are known for their mild sedative, euphoric, and aphrodisiac effects. Blue lotus has been traditionally used in ancient Egyptian medicine for spiritual and recreational purposes.
  28. Henbane (Hyoscyamus niger) Henbane is a plant native to Europe, Asia, and North Africa, containing psychoactive compounds hyoscyamine (0.03-0.2%) and scopolamine (0.01-0.08%). These compounds are known for their sedative, deliriant, and hallucinogenic effects. Henbane has been traditionally used in European herbal medicine for pain and insomnia, but its use is not recommended due to its high toxicity.
  29. Mandrake (Mandragora officinarum) Mandrake is a perennial herbaceous plant native to the Mediterranean region, containing psychoactive compounds hyoscyamine (0.2-0.5%) and scopolamine (0.1-0.4%). These compounds are known for their sedative, deliriant, and hallucinogenic effects. Mandrake has been traditionally used in European herbal medicine for pain and surgical anesthesia, but its use is not recommended due to its high toxicity.
  30. Datura (Datura stramonium) Datura is a herbaceous plant native to North America, containing psychoactive compounds atropine (0.2-0.6%) and scopolamine (0.1-0.5%). These compounds are known for their deliriant, hallucinogenic, and amnestic effects. Datura has been traditionally used in Native American medicine for spiritual and ritualistic purposes, but its use is not recommended due to its high toxicity and potential for severe adverse effects.
  31. Brugmansia (Brugmansia spp.) Brugmansia is a genus of flowering plants native to South America, containing psychoactive compounds scopolamine (0.2-0.6%) and hyoscyamine (0.1-0.4%). These compounds are known for their deliriant, hallucinogenic, and amnestic effects. Brugmansia has been traditionally used in South American shamanic practices, but its use is not recommended due to its high toxicity and potential for severe adverse effects.
  32. Coleus (Coleus blumei) Coleus is a perennial herb native to Southeast Asia, containing the psychoactive compound forskolin (0.1-0.5%). Forskolin is known for its ability to increase cAMP levels, which may lead to potential weight loss and cognitive enhancement effects. Coleus has been traditionally used in Ayurvedic medicine for heart and lung disorders and has been the subject of research for its potential applications in weight loss and cognitive function.
  33. Periwinkle (Catharanthus roseus) Periwinkle is a perennial herb native to Madagascar, containing psychoactive compounds vinblastine (0.01-0.03%) and vincristine (0.0003-0.001%). These compounds are known for their antineoplastic effects and potential cognitive-enhancing properties. Periwinkle has been traditionally used in Malagasy traditional medicine and has been the subject of extensive research for its applications in cancer chemotherapy.
  34. Iboga (Tabernanthe iboga) Iboga is a shrub native to West Africa, containing the psychoactive compound ibogaine (0.5-6%). Ibogaine is known for its intense psychedelic effects, introspection, and potential anti-addictive properties. Iboga has been traditionally used in the Bwiti spiritual practice in West Africa and has been the subject of research for its potential applications in the treatment of addiction.
  35. Yopo (Anadenanthera peregrina) Yopo is a perennial tree native to South America, containing psychoactive compounds bufotenin (0.04-0.16%) and DMT (0.1-0.6%). These compounds are known for their intense psychedelic effects, introspection, and spiritual experiences. Yopo has been traditionally used by indigenous groups in South America for spiritual and ritualistic purposes.
  36. Sinicuichi (Heimia salicifolia) Sinicuichi is a shrub native to Mexico and Central America, containing psychoactive compounds cryogenine (0.1-0.5%) and lythrine (0.05-0.3%). These compounds are known for their mild psychedelic effects and auditory hallucinations. Sinicuichi has been traditionally used by indigenous groups in Mexico for spiritual and ritualistic purposes.
  37. Acacia (Acacia spp.) Acacia is a genus of shrubs and trees native to Australia, Africa, and the Americas, containing psychoactive compounds DMT (0.1-0.5%), mescaline (0.05-0.2%), and NMT (0.05-0.2%). These compounds are known for their psychedelic effects, altered perception, and spiritual experiences. Acacia has been traditionally used by indigenous groups in Australia and Africa for spiritual and ritualistic purposes.
  38. Syrian Rue (Peganum harmala) Syrian rue is a perennial herbaceous plant native to the Middle East, North Africa, and Central Asia, containing psychoactive compounds harmine (2-7%), harmaline (0.2-1.7%), and tetrahydroharmine (0.1-0.5%). These compounds are known for their mild psychedelic effects, MAO inhibition, and potential synergy with other psychedelics. Syrian rue has been traditionally used in Middle Eastern and North African cultures for spiritual and medicinal purposes.
  39. San Pedro cactus (Trichocereus pachanoi) San Pedro cactus is a columnar cactus native to the Andes, containing the psychoactive compound mescaline (0.2-2%). Mescaline is known for its visual hallucinations, altered perception and consciousness, and spiritual experiences. San Pedro cactus has been traditionally used by indigenous groups in South America for spiritual and medicinal purposes.
  40. Jurema (Mimosa tenuiflora) Jurema is a tree native to Brazil, containing the psychoactive compound DMT (0.5-1.5%). DMT is known for its intense psychedelic effects, altered perception, and spiritual experiences. Jurema has been traditionally used by indigenous groups in Brazil for spiritual rituals.
  41. Wild Dagga (Leonotis leonurus) Wild dagga is a perennial shrub native to South Africa, containing the psychoactive compound leonurine (0.1-0.5%). Leonurine is known for its mild psychoactive effects, sedation, and euphoria. Wild dagga has been traditionally used in South Africa for medicinal and recreational purposes.
  42. Dream Herb (Calea zacatechichi) Dream herb is a shrub native to Mexico and Central America, containing the psychoactive compound caleine (0.05-0.2%). Caleine is known for its ability to induce vivid dreams and mild psychoactive effects. Dream herb has been traditionally used by indigenous groups in Mexico for dream enhancement and divination.
  43. African Dream Root (Silene capensis) African dream root is a perennial herb native to South Africa, containing triterpenoid saponins (0.1-0.5%). These compounds are known for their ability to induce vivid dreams and mild psychoactive effects. African dream root has been traditionally used by the Xhosa people in South Africa for dream enhancement and spiritual purposes.
  44. Snowdrop (Galanthus nivalis) Snowdrop is a perennial herbaceous plant native to Europe and the Middle East, containing the psychoactive compound galantamine (0.1-0.5%). Galantamine is known for its acetylcholinesterase inhibition and potential cognitive-enhancing effects. Snowdrop has been approved for the treatment of Alzheimer's disease and other cognitive disorders.
  45. Toothed Clubmoss (Huperzia serrata) Toothed clubmoss is a perennial herb native to China and Southeast Asia, containing the psychoactive compound huperzine A (0.01-0.1%). Huperzine A is known for its acetylcholinesterase inhibition and potential cognitive-enhancing effects. Toothed clubmoss has been traditionally used in Chinese medicine for cognitive disorders and has been the subject of research for its potential applications in the treatment of Alzheimer's disease.
  46. Brahmi (Bacopa monnieri) Brahmi is a perennial creeping herb native to India and Southeast Asia, containing psychoactive compounds bacoside A (2-5%) and bacoside B (1-3%). These compounds are known for their cognitive-enhancing, neuroprotective, and anxiolytic effects. Brahmi has been traditionally used in Ayurvedic medicine for cognitive disorders and anxiety and has been the subject of research for its potential applications in the treatment of cognitive function.
  47. Gotu Kola (Centella asiatica) Gotu kola is a perennial herbaceous plant native to India and Southeast Asia, containing psychoactive compounds asiaticoside (0.1-0.8%) and madecassoside (0.1-0.6%). These compounds are known for their cognitive-enhancing, anxiolytic, and wound-healing effects. Gotu kola has been traditionally used in Ayurvedic and Chinese medicine for cognitive disorders and skin conditions and has been the subject of research for its potential applications in the treatment of cognitive function and wound healing.
  48. Changa (combination of DMT-containing plants and MAOI-containing plants) Changa is a smoking blend containing a combination of DMT-containing plants and MAOI-containing plants, such as Banisteriopsis caapi and Psychotria viridis. The concentration of psychoactive compounds varies based on the specific combination of plants used. Changa is known for its intense psychedelic effects, altered perception, and spiritual experiences. It has no approved medical use and is used in some spiritual and recreational contexts.
  49. Intellect Tree (Celastrus paniculatus) Intellect tree is a climbing shrub native to India, containing psychoactive compounds celastrine (0.1-0.5%) and paniculatine (0.05-0.3%). These compounds are known for their cognitive-enhancing, neuroprotective, and anxiolytic effects. Intellect tree has been traditionally used in Ayurvedic medicine for cognitive disorders and anxiety and has been the subject of research for its potential applications in the treatment of cognitive function.
  50. Ginkgo (Ginkgo biloba) Ginkgo is a tree native to China, containing psychoactive compounds ginkgolides (0.06-0.2%) and bilobalide (0.13-0.5%). These compounds are known for their cognitive-enhancing, neuroprotective, and circulatory-improving effects. Ginkgo has been used in traditional Chinese medicine for cognitive disorders and has been approved for the treatment of dementia and cognitive disorders in some countries. It has been the subject of extensive research for its potential applications in the treatment of cognitive function and Alzheimer's disease.
  51. Golden Root (Rhodiola rosea) Golden root is a perennial herbaceous plant native to the Arctic regions of Europe, Asia, and North America, containing psychoactive compounds salidroside (0.5-2%) and rosavin (1-3%). These compounds are known for their adaptogenic, stress-reducing, and cognitive-enhancing effects. Golden root has been traditionally used in Scandinavian and Russian medicine for stress and fatigue and has been the subject of research for its potential applications in the treatment of stress and cognitive function.
  52. Kanna (Sceletium tortuosum) Kanna is a succulent plant native to South Africa, containing psychoactive compounds mesembrine (0.3-1%) and mesembrenone (0.1-0.5%). These compounds are known for their mood-enhancing, mildly euphoric, and anxiolytic effects. Kanna has been traditionally used by the San and Khoikhoi people in South Africa for stress and mood and has been the subject of research for its potential applications in the treatment of depression and anxiety.
  53. Voacanga (Voacanga africana) Voacanga is a small tree native to West Africa, containing psychoactive compounds voacamine (0.1-0.5%) and voacangine (0.05-0.3%). These compounds are known for their mild psychedelic effects, stimulation, and euphoria. Voacanga has been traditionally used in West African medicine for various ailments and has been the subject of research for its potential anti-addictive properties.
  54. Guayusa (Ilex guayusa) Guayusa is a tree native to the Amazon rainforest, containing psychoactive compounds caffeine (1.5-3%) and theobromine (0.1-0.5%). These compounds are known for their stimulating effects, increased alertness, and improved cognitive function. Guayusa has been traditionally used by indigenous groups in the Amazon for energy and mental clarity.
  55. Cacao (Theobroma cacao) Cacao is a small tree native to Mesoamerica and South America, containing psychoactive compounds theobromine (1-4%) and caffeine (0.1-0.7%). These compounds are known for their mild stimulating effects, mood enhancement, and antioxidant properties. Cacao has been traditionally used by indigenous groups in Mesoamerica for medicinal and cultural purposes and has been the subject of research for its potential applications in cardiovascular health and cognitive function.
  56. Roselle (Hibiscus sabdariffa) Roselle is a flowering plant native to Africa and Southeast Asia, containing anthocyanins (1-2%) and organic acids (15-30%). These compounds are known for their mild sedative, anxiolytic, and antioxidant properties. Roselle has been traditionally used in African and Asian medicine for hypertension and anxiety and has been the subject of research for its potential applications in cardiovascular health and stress relief.
  57. Linden (Tilia spp.) Linden is a genus of trees native to Europe and North America, containing psychoactive compounds tiliroside (0.1-0.5%) and kaempferol (0.05-0.2%). These compounds are known for their mild sedative, anxiolytic, and anti-inflammatory properties. Linden has been traditionally used in European medicine for anxiety and sleep disorders and has been the subject of research for its potential applications in anxiety and inflammation.
  58. Lemon Balm (Melissa officinalis) Lemon balm is a perennial herbaceous plant native to Europe, North Africa, and West Asia, containing psychoactive compounds rosmarinic acid (0.5-4%) and linalool (0.1-0.5%). These compounds are known for their mild sedative, anxiolytic, and cognitive-enhancing effects. Lemon balm has been traditionally used in European medicine for anxiety and cognitive disorders and has been the subject of research for its potential applications in anxiety and cognitive function.
  59. Sângue de Cristo (Justicia pectoralis) Sângue de Cristo is a perennial herb native to South America, containing the psychoactive compound coumarin (0.1-0.5%). Coumarin is known for its mild sedative, anxiolytic, and anti-inflammatory properties. Sângue de Cristo has been traditionally used in South American medicine for anxiety and respiratory disorders and has been the subject of research for its potential applications in anxiety and inflammation.
  60. Saffron (Crocus sativus) Saffron is a perennial flowering plant native to the Middle East and Mediterranean region, containing psychoactive compounds crocin (5-15%) and safranal (0.1-0.5%). These compounds are known for their mild sedative, mood-enhancing, and cognitive-enhancing effects. Saffron has been traditionally used in Middle Eastern and Mediterranean medicine for mood disorders and cognitive enhancement and has been the subject of research for its potential applications in depression and cognitive function.
  61. Reed Canary Grass (Phalaris arundinacea) Reed canary grass is a perennial grass native to temperate regions worldwide, containing psychoactive compounds DMT (0.01-0.05%) and 5-MeO-DMT (0.002-0.01%). These compounds are known for their mild psychedelic effects and potential synergy with other psychedelics. Reed canary grass has no approved medical use and is used in some spiritual and recreational contexts.
  62. Chacruna (Psychotria viridis) Chacruna is a shrub native to the Amazon rainforest, containing the psychoactive compound DMT (0.1-0.66%). DMT is known for its intense psychedelic effects, altered perception, and spiritual experiences when used in combination with MAO inhibitors. Chacruna has been traditionally used by indigenous groups in the Amazon for spiritual and medicinal purposes and has been the subject of research for its potential therapeutic applications.
  63. Chaliponga (Diplopterys cabrerana) Chaliponga is a perennial vine native to the Amazon rainforest, containing psychoactive compounds DMT (0.1-0.5%) and 5-MeO-DMT (0.05-0.2%). These compounds are known for their intense psychedelic effects, altered perception, and spiritual experiences when used in combination with MAO inhibitors. Chaliponga has been traditionally used by indigenous groups in the Amazon for spiritual and medicinal purposes.
  64. African Peach (Nauclea latifolia) African peach is a small tree native to West and Central Africa, containing psychoactive compounds known as naucleamides A-E (0.1-0.5%). These compounds are known for their mild sedative, anxiolytic, and anti-inflammatory properties. African peach has been traditionally used in African medicine for anxiety, pain, and inflammation.
  65. Skullcap (Scutellaria lateriflora) Skullcap is a perennial herbaceous plant native to North America, Europe, and China, containing psychoactive compounds baicalin (1-5%) and baicalein (0.1-0.5%). These compounds are known for their mild sedative, anxiolytic, and anti-inflammatory properties. Skullcap has been traditionally used in North American and Chinese medicine for anxiety and inflammation and has been the subject of research for its potential applications in anxiety and neuroprotection.
  66. California Poppy (Eschscholzia californica) California poppy is a perennial herbaceous plant native to western North America, containing psychoactive compounds californidine (0.1-0.5%) and protopine (0.05-0.2%). These compounds are known for their mild sedative, anxiolytic, and analgesic properties. California poppy has been traditionally used by Native American groups for pain and anxiety and has been the subject of research for its potential applications in anxiety and pain relief.
  67. Wild Lettuce (Lactuca virosa) Wild lettuce is a biennial herbaceous plant native to Europe, North Africa, and West Asia, containing the psychoactive compound lactucin (0.05-0.2%). Lactucin is known for its mild sedative and analgesic properties. Wild lettuce has been traditionally used in European medicine for pain and insomnia.
  68. Vervain (Verbena officinalis) Vervain is a perennial herbaceous plant native to Europe, North Africa, West Asia, and North America, containing psychoactive compounds verbenin (0.05-0.2%) and hastatoside (0.1-0.5%). These compounds are known for their mild sedative, anxiolytic, and anti-inflammatory properties. Vervain has been traditionally used in European and North American medicine for anxiety and inflammation.
  69. Jamaican Dogwood (Piscidia piscipula) Jamaican dogwood is a tree native to the Caribbean and Central America, containing the psychoactive compound rotenone (0.1-0.5%). Rotenone is known for its mild sedative, analgesic, and antispasmodic properties. Jamaican dogwood has been traditionally used in Caribbean medicine for pain and spasms.
  70. Oat (Avena sativa) Oat is an annual grass cultivated worldwide, containing psychoactive compounds known as avenanthramides (0.01-0.1%). These compounds are known for their mild sedative, anxiolytic, and anti-inflammatory properties. Oat has been traditionally used in European medicine for anxiety and stress relief and has been the subject of research for its potential applications in anxiety and inflammation.
  71. Hops (Humulus lupulus) Hops is a perennial climbing plant native to Europe and North America, containing psychoactive compounds humulone (0.5-3%) and lupulone (0.5-2%). These compounds are known for their mild sedative, anxiolytic, and anti-inflammatory properties. Hops has been traditionally used in European medicine for anxiety and sleep disorders and is used in the brewing of beer for flavoring and preservation.
  72. Griffonia (Griffonia simplicifolia) Griffonia is a shrub native to West and Central Africa, containing the psychoactive compound 5-HTP (5-Hydroxytryptophan) (2-20%). 5-HTP is known for its mood-enhancing effects and ability to increase serotonin production. Griffonia is used as a dietary supplement for mood support and sleep and has been the subject of research for its potential applications in the treatment of depression and anxiety.
  73. Black Pepper (Piper nigrum) Black pepper is a flowering vine native to India and Southeast Asia, containing the psychoactive compound piperine (1-4%). Piperine is known for its mild stimulating effects, cognitive enhancement, and ability to increase the bioavailability of other compounds. Black pepper has been traditionally used in Ayurvedic and other traditional medicine systems for digestive health and cognitive enhancement and has been the subject of research for its potential applications in cognitive function and nutrient absorption.
  74. Galangal (Alpinia galanga) Galangal is a rhizomatous herbaceous plant native to Southeast Asia, containing psychoactive compounds 1,8-cineole (20-30%) and galangin (0.1-0.5%). These compounds are known for their mild stimulating effects, cognitive enhancement, and anti-inflammatory properties. Galangal has been traditionally used in Ayurvedic and Southeast Asian medicine for cognitive enhancement and inflammation and has been the subject of research for its potential applications in cognitive function and inflammatory conditions.
  75. Licorice (Glycyrrhiza glabra) Licorice is a perennial herbaceous plant native to Europe, Asia, and North Africa, containing the psychoactive compound glycyrrhizin (2-15%). Glycyrrhizin is known for its mild sedative, anti-inflammatory, and antiviral properties. Licorice has been traditionally used in Ayurvedic, Chinese, and European medicine for respiratory and digestive disorders and has been the subject of research for its potential applications in inflammation and viral infections.
  76. Guduchi (Tinospora cordifolia) Guduchi is a deciduous climbing shrub native to India and Sri Lanka, containing psychoactive compounds berberine (0.1-0.5%) and tinosporin (0.05-0.2%). These compounds are known for their adaptogenic, immune-enhancing, and cognitive-enhancing effects. Guduchi has been traditionally used in Ayurvedic medicine for immune support and cognitive enhancement and has been the subject of research for its potential applications in immune function and cognitive performance.
  77. Turmeric (Curcuma longa) Turmeric is a rhizomatous herbaceous plant native to India and Southeast Asia, containing the psychoactive compound curcumin (2-8%). Curcumin is known for its anti-inflammatory, antioxidant, and cognitive-enhancing effects. Turmeric has been traditionally used in Ayurvedic and Chinese medicine for inflammatory conditions and cognitive enhancement and has been the subject of extensive research for its potential applications in inflammation, brain health, and various chronic diseases.
  78. Jiaogulan (Gynostemma pentaphyllum) Jiaogulan is a perennial climbing vine native to China and Southeast Asia, containing psychoactive compounds known as gypenosides (2-3%). These compounds are known for their adaptogenic, anti-aging, and cognitive-enhancing effects. Jiaogulan has been traditionally used in Chinese medicine for longevity and cognitive enhancement and has been the subject of research for its potential applications in cognitive function and metabolic health.
  79. Schisandra (Schisandra chinensis) Schisandra is a deciduous woody vine native to China, Russia, and Korea, containing psychoactive compounds known as schisandrins, including schisandrin A and schisandrin B (0.5-2%). These compounds are known for their adaptogenic, hepatoprotective, and cognitive-enhancing effects. Schisandra has been traditionally used in Chinese medicine for liver health and cognitive enhancement and has been the subject of research for its potential applications in liver function and cognitive performance.
  80. Siberian Ginseng (Eleutherococcus senticosus) Siberian ginseng is a deciduous shrub native to northeastern Asia, containing psychoactive compounds known as eleutherosides (0.6-0.9%). These compounds are known for their adaptogenic, immune-enhancing, and cognitive-enhancing effects. Siberian ginseng has been traditionally used in Chinese and Russian medicine for stress resistance and cognitive enhancement and has been the subject of research for its potential applications in stress, immune function, and cognitive performance.
  81. Red Sage (Salvia miltiorrhiza) Red sage is a perennial plant native to China, containing psychoactive compounds known as tanshinones, including tanshinone I and tanshinone IIA (0.2-0.5%). These compounds are known for their neuroprotective, cognitive-enhancing, and cardiovascular health-promoting effects. Red sage has been traditionally used in Chinese medicine for cardiovascular and cognitive health and has been the subject of research for its potential applications in brain and heart health.
  82. Yuan Zhi (Polygala tenuifolia) Yuan Zhi is a perennial herbaceous plant native to China and Korea, containing psychoactive compounds known as saponins, including tenuifolin and tenuifoliside A (2-4%). These compounds are known for their neuroprotective, cognitive-enhancing, and anxiolytic effects. Yuan Zhi has been traditionally used in Chinese medicine for cognitive and emotional well-being and has been the subject of research for its potential applications in cognitive function and anxiety.
  83. Tianma (Gastrodia elata) Tianma is a perennial orchid native to China, Korea, and Japan, containing psychoactive compounds gastrodin (0.2-0.7%) and 4-hydroxybenzyl alcohol (0.1-0.5%). These compounds are known for their neuroprotective, cognitive-enhancing, and anticonvulsant effects. Tianma has been traditionally used in Chinese medicine for neurological disorders and cognitive health and has been the subject of research for its potential applications in brain health and epilepsy.
  84. Cat's Claw (Uncaria tomentosa) Cat's claw is a woody vine native to the Amazon rainforest, containing psychoactive compounds known as pentacyclic oxindole alkaloids (POAs), such as pteropodine and isopteropodine (0.5-1.5%). These compounds are known for their immune-enhancing, anti-inflammatory, and neuroprotective effects. Cat's claw has been traditionally used in South American medicine for immune support and inflammatory conditions and has been the subject of research for its potential applications in immune function, inflammation, and brain health.
  85. Maca (Lepidium meyenii) Maca is a perennial herbaceous plant native to the Andes mountains of Peru, containing psychoactive compounds known as glucosinolates, such as benzyl glucosinolate (0.1-0.5%), and macamides (0.05-0.2%). These compounds are known for their adaptogenic, hormone-balancing, and cognitive-enhancing effects. Maca has been traditionally used in Peruvian medicine for fertility and cognitive health and has been the subject of research for its potential applications in hormonal balance, cognitive function, and physical performance.

The A-Z List Of Compounds

If you're a chemist, you'll want to dive right into IUPAC and SMILES. If you're not familiar with SMILES (the strange list of characters with Cs and Os), it's a way of representing 3D chemical molecules as a line of text, which you can also store in a database.

You can go here and paste some of them in to look at them visually: https://www.cheminfo.org/Chemistry/Cheminformatics/Smiles/index.html

  1. 1,8-Cineole: CC12CCC(CC1)C(C)(C)O2
  2. 4-Hydroxybenzyl alcohol: OCC1=CC=C(O)C=C1
  3. 5-HTP (5-Hydroxytryptophan): NC(CC1=CNC2=C1C=C(O)C=C2)C(O)=O
  4. 5-MeO-DMT: COC1=CC2=C(C=C1)N(C)CC2CCN
  5. 7-Hydroxymitragynine: CC(C)=CCN1CC2=C(C1)C=C(OC)C(O)=C2C1=COC3=C(C1=O)C(OC)=C(O)C=C3
  6. Apomorphine: CN1CCc2cccc(O)c2C1
  7. Arecoline: CN1CCC2=CC(=O)C=CC2=C1
  8. Asiaticoside: CC1C(C(C(C(O1)OC2C(C(C(C(O2)CO)O)O)O)OC3C(C(C(CO3)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)C(=O)O)O)O)O)O)O)O)O
  9. Atropine: CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
  10. Avenanthramides: OC(Cc1ccc(O)cc1)C(N)Cc2ccc(O)cc2
  11. Bacoside A: CC1(C)CCC2(C(=O)C3(C)CCC4(C(C3C2C1O)CCC5C4(CCC(C5(C)C)O)C)C)O
  12. Bacoside B: CC1(C)CCC2(C(C1O)CCC3(C2CCC4C3(CCC(C4(C)C=O)O)C)C)O
  13. Baicalein: O=C1C=C(O)C2=C(C=C(O)C=C2)O1
  14. Baicalin: OC1=CC=C(C2=CC(=O)C3=C(O)C(O)=C(O)C=C3O2)C=C1
  15. Benzyl glucosinolate: OC1OC(CO)C(O)C(O)C1SC(=N)NC(Cc1ccccc1)C(=O)O
  16. Berberine: COC1=CC2=C(C=C1)C1=CC3=C(CN2)C4=C(C=CC(OC)=C4)O3
  17. Bilobalide: CC1(C)C2CCC3(C(C2C4(C1=O)C(=O)C(C(C4)O)O)CC(C3)O)C
  18. Bufotenin: CN(C)CCC1=CNC2=C1C=C(O)C=C2
  19. Caffeine: Cn1cnc2c1c(=O)n(C)c(=O)n2C
  20. Caleine: C=C1C(CC2CN3CCCC3C12)OC(=O)C
  21. Californidine: CN1CCc2cc3c(cc2C1)OCO3
  22. Cathine: NC(C(O)c1ccccc1)C(O)c1ccccc1
  23. Cathinone: CCNC(C)C(=O)c1ccccc1
  24. CBD (Cannabidiol): CCCCCc1cc(O)c2c(c1)OC(C)(C)C1CCC(C)=CC21
  25. Celastrine: CC(C)=CCCC(C)=CC1CCC2(C)C3CCC4C(C3(CCC2C1)C)CCC5(C)C(C4C(=O)OC)CC(OC(=O)C)CC5OC(=O)C
  26. Cocaine: COC(=O)C1C(OC(=O)c2ccccc2)CC2CCC1N2C
  27. Codeine: COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)C@@HN(C)CC[C@]314
  28. Coumarin: O=C1Oc2ccccc2C=C1
  29. Crocin: OCC1OC(Oc2cc(CO)c3c(O)cc(C4=CC(=O)C5=C(O)C=C(O)C=C5O4)cc3c2)C(O)C(O)C1O
  30. Cryogenine: CN1CCc2cc3c(cc2C1)OCO3
  31. Curcumin: COc1cc(/C=C/C(=O)CC(=O)/C=C/c2ccc(O)c(OC)c2)ccc1O
  32. Damianin: CC1CCC2C(C1)C(=O)OC2(C)C
  33. Desmethoxyyangonin: C=CCc1coc2c1C(=O)C(OC)=CC2
  34. Dihydrokavain: CCCC1COC2=C1C(=O)C=C(OC)C2
  35. Dihydromethysticin: COc1ccc(cc1OC)C1COC2=C1C(=O)C=CC2
  36. DMT (N,N-Dimethyltryptamine): CN(C)CCc1c[nH]c2ccccc12
  37. Ephedrine: CNC(C)C(O)c1ccccc1
  38. Ergine (LSA): CN1CC(C=C2C1Nc1ccccc1N2)C(=O)NC1C=CC=CC=1
  39. Forskolin: CC1(C)CCC2(C(O1)C1C(CC3C(O)CC(=O)C(C)(C)C3C(O)C1)OC1OC21)C
  40. Galantamine: COc1ccc2c3c1O[C@H]1CC(=O)C[C@@H]4Oc5c(O)ccc(c53)[C@@]14N2C
  41. Galangin: Oc1ccc(cc1)C1=COc2cc(O)cc(O)c2C1=O
  42. Gastrodin: OCCc1ccc(O)cc1OC1OC(CO)C(O)C(O)C1O
  43. Ginkgolides (A, B, C, J): CC1(C)C2CCC3(C(C2C4(C1O)C(OC(=O)C(O)(C4)CO)O)CC(C3O)O)C
  44. Glycyrrhizin: C[C@H]1C@@HO
  45. Gonzalitosin I: CC1CCC2C(C1)C(=O)OC2(C)C
  46. Gypenosides: CC1C(OC2OC(COC3OC(CO)C(O)C(O)C3O)C(O)C(O)C2O)OC2C(O)C(O)C3OCC(O)(C(C3C2O)O)C(C=CC(C)C1O)O
  47. Harmaline: COc1ccc2c3c1[nH]c1c(C2=O)c(C)nc(C)c13
  48. Harmine: COc1ccc2c3c1[nH]c1c(C2=O)cnc(C)c13
  49. Hastatoside: OCC1OC(Oc2cc(O)cc(O)c2C(=O)O)C(O)C(O)C1O
  50. Humulone: CC(C)C1CC(=O)C(=C(O)C1)CC=C(C)C
  51. Huperzine A: CC1=NC(Cc2ccccc2)C2C(=O)N3C(CCC3C2=O)C1=O
  52. Hypericin: OC1=CC(O)=C2C=C3C4=C(C(O)=CC(O)=C4C(O)=C3OC2=C1)C(O)=C5OC6=C(C(O)=C(O)C=C6C(O)=C5O)C(O)=C1C=C(O)C(O)=C3C1=C7C(O)=CC(O)=C8C9=C(C(O)=CC(O)=C9C(O)=C8OC3=C7)C(O)=CC(O)=C1O
  53. Hyperforin: CC1=CC(=O)C(C(C)(C)CCC=C(C)C)CC1CCC(C)=CCCC(OC2=CC3=C(CCC3(C)C)C(O)=C2)C(C)(C)O
  54. Hyoscyamine: CN1C2CCC1CC(C2)OC(=O)C(CO)c1ccccc1
  55. Ibogaine: CCC1CC2CC3CC1N(C2)CCc1c3[nH]c2ccccc12
  56. Isoergine: CN1CC(C=C2C1Nc1ccccc1N2)C(=O)Nc1ccccc1
  57. Isopteropodine: COc1cc2c3c4ccnc(c4c[nH]c3c1OC)C2
  58. Isovaleric acid: CC(C)CC(O)=O
  59. Kavain: O=C1C=C(OC)C2=C1C(c1ccccc1)OC2
  60. Lactucin: CC1=C(C(=O)C=C2C1=CC(=O)OC2(C)C)C=CC(C)C
  61. Leonurine: COc1c(O)cc2c(c1OC)C(=O)N(C2)C(=O)OC
  62. Linalool: CC(C)=CCCC(C)(O)C=C
  63. Lophophine: COc1cc2c3c(c1O)C1(CC3)CC(O)C(C(C)C)CN1CC2
  64. Lupulone: CC(C)C1CC(=O)C(=C(O)C1)CCC(C)(C)O
  65. Lythrine: CN1CCc2cc3c(cc2C1CC=C(C)C)OCO3
  66. Macamides: CCCCCCCCC(=O)NCCCC(O)C1C=C(OC)C(OC)=C(OC)C1
  67. Madecassoside: OCC1OC(OC2C(O)C(OC3OC(C(=O)O)C(O)C(O)C3O)OCC2OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O
  68. Mescaline: COc1cc(CCN)cc(OC)c1OC
  69. Mesembrenone: COc1c2ccoc2cc2c1[nH]cc2C(C)=O
  70. Mesembrine: COc1c2ccoc2cc2c1[nH]cc2C(C)C
  71. Methysticin: COc1ccc(cc1OC)C1COC2=C1C(=O)C(OC)=CC2
  72. Mitragynine: CN1CCc2c([nH]c3ccccc23)[C@H]2C[C@H]1C[C@H]3C@HN(C)c1ccccc13
  73. Morphine: CN1CC[C@@]2(C[C@@H]1C[C@@H]3c4ccccc4CC(=O)O3)c1ccccc12
  74. Muirapuamine: CN1CCc2cc3c(cc2C1C1COC2=C1C(=O)C=CC2)OCO3
  75. Muirapuamine A: CN1CCc2cc3c(cc2C1C1COC2=C1C(=O)C(OC)=CC2)OCO3
  76. Naucleamides A-E: CC(C)(C)C(=O)N1CCc2c1[nH]c1ccccc21
  77. Nepetalactone: CC1=CCC(CC1)C(C)(C)O
  78. Nicotine: CN1CCC[C@H]1c1cccnc1
  79. NMT (N-methyltryptamine): CNc1ccccc1CCc1c[nH]c2ccccc12
  80. Nuciferine: COc1ccc2c(c1)OC[C@@H]1NCCc3c1[nH]c1ccccc31-2
  81. Paniculatine: CC(C)=CCCC(C)=CC1CCC2(C)C3CCC4C(C3(CCC2C1)C)CCC5(C)C(C4C(OC)=O)CC(OC(C)=O)CC5OC(C)=O
  82. Piperine: O=C(C=CC1=CC=C2OCO2C1)/N1CCCC1
  83. Protopine: O=C1c2ccccc2[C@@H]2c3c(cc4OCOc4c3O)[C@H]3NCCc1c23
  84. Pseudoephedrine: CC(NC)C(O)c1ccccc1
  85. Psilocin: Cn1cc(C(O)C2CCNC2)c2ccccc21
  86. Psilocybin: Cn1cc(C(OP(O)(O)=O)C2CCNC2)c2ccccc21
  87. Pteropodine: COc1cc2c3c4ccnc(c4c[nH]c3c1O)C2
  88. Reserpine: COC(=O)[C@@H]1[C@H]2CCC@(C(=O)OC)[C@]1(C)CC[C@@H]1[C@@H]2C(=O)OC2=C1C=C(OC)C1=C2NC[C
  89. Rosmarinic acid: O=C(O)/C=C/c1ccc(O)c(O)c1/C=C/C(=O)OC(Cc1ccc(O)c(O)c1)C(=O)O
  90. Rotenone: COc1cc(C2OC3=C(COC3=O)C2c2cc(OC)c(OC)c(OC)c2)ccc1O
  91. Safranal: CC(=O)/C=C/C1=C(C)C=CCC1(C)C
  92. Salidroside: OC[C@H]1OC@@HC@HC@@H[C@@H]1O
  93. Salvinorin A: CC(=O)O[C@@H]1Cc2ccc(OC(=O)C34C[C@@H]5CC@HC(=O)O[C@H]5C@HOC(C)=O)cc2OC1=O
  94. Saponins (Tenuifolin, Tenuifoliside A): CC1OC(OC2C(C)OC(OC3CCC4(C)C(CCC5C4CCC4(C)C(CCC45C)C(O)=O)C3)OC2C)C(O)C(O)C1O
  95. Schisandrins (Schisandrin A, Schisandrin B): COc1cc2c(cc1OC)C@HC@@Hc1c(OC)cc(cc1OC)CC@@H[C@H]2C
  96. Scopolamine: CN1C2CC(CC1C(=O)OC(CO)c1ccccc1)C1C(C2)CC@@HC[C@@H]1OC(=O)C(CO)c1ccccc1
  97. Tanshinones (Tanshinone I, Tanshinone IIA): CC1COC2=C1C(=O)C(=O)c1c2ccc2c1CCCC2(C)C
  98. Tetrahydroharmine: CN1CCc2c3ccccc3n(C)c2C1
  99. THC (Δ9-tetrahydrocannabinol): CCCCCC1=CC(=C2C3C=C(CCC3C(O)C=C2C1)C)C
  100. Thebaine: COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)C@@HN(C)CC[C@]314
  101. Theobromine: Cn1cnc2c1c(=O)[nH]c(=O)n2C
  102. Tiliroside: O=C(c1c(O)cc(O)cc1OC1OC(CO)C(O)C(O)C1O)c1ccc(O)cc1
  103. Tinosporin: COc1ccc2c(c1)C[C@@H]1c3cc(OC)c(OC)cc3CCN1CC2
  104. Triterpenoid saponins: CC(C)C1CCC2(C)CCC3(C)C(=CCC4C3(CCC5(C)C(C(O)CC5(C)C)CC(O)C4C(C)C)C)C2C1C
  105. Valerenic acid: CC(C)C1CCC(C(C)C)C(CC=C(C)C(=O)O)C1
  106. Verbenin: O=C(OC1Cc2ccc(O)cc2OC1c1ccc(O)c(O)c1)c1ccc(O)cc1
  107. Vertine: CN1CCc2cc3c(cc2C1Cc1ccccc1)OCO3
  108. Vinblastine: CCC(=O)O[C@H]1[C@H](C@HOC(=O)C
  109. Vincristine: CCC(=O)O[C@H]1[C@H](C@HOC(=O)C
  110. Voacamine: CC[C@H]1CN2CCc3c([nH]c4cccc(OC)c34)[C@H]2C[C@H]1C[C@H]1NCCc2c1[nH]c1ccccc21
  111. Voacangine: CC[C@H]1CN2CCc3c([nH]c4cccc(OC)c34)[C@H]2C[C@H]1C[C@@H]1NCCc2c1[nH]c1ccc(OC)cc21
  112. Withanolides (Withaferin A, Withanolide A): CC(=O)OC1CCC2(C)C(=CCC3C2CCC2(C)C(C(=O)C(O)C2)CCC34C)C14C
  113. Yangonin: C=CCc1coc2c1C(=O)C(OC)=C(OC)C2
  114. Yohimbine: COC(=O)[C@@H]1[C@H]2CCC@(C(=O)OC)[C@]1(C)CC[C@@H]1[C@@H]2C=CC2=C1NC[C@H]1C3=CC=CC=C3C@@HC1

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