Harmaline: Difference between revisions

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'''Harmaline''', also known as '''7-methoxyharmalan''' or as '''3,4-dihydro-7-methoxy-1-methyl-β-carboline''', is a [[fluorescent]] [[indole]] [[alkaloid]] from the group of [[harmala alkaloid]]s and [[substituted β-carboline|β-carboline]]s.<ref name="BrimblecombePinder1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | title = Hallucinogenic Agents | location = Bristol | pages = 98–144 | date = 1975 | publisher = Wright-Scientechnica | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1 | quote = [...] the apparent superiority of extracts of Banisteriopsis over the pure harmine prompted the suggestion (Hochstein and Paradies, 1957) that either harmaline or 1,2,3,4-tetrahydroharmine, or other as then unidentified constituents, were the psychoactive compounds. Naranjo (1967) has now confirmed their hallucinogenic activity in man together with that of 6-methoxyharmalan and 6-methoxytetrahydroharman. [...]}}</ref><ref name="Shulgin1977">{{cite journal | last=Shulgin | first=Alexander T. | title=Profiles of Psychedelic Drugs: 4. Harmaline | journal=Journal of Psychedelic Drugs | volume=9 | issue=1 | date=1977 | issn=0022-393X | doi=10.1080/02791072.1977.10472029 | pages=79–80 | url=https://www.tandfonline.com/doi/full/10.1080/02791072.1977.10472029 | access-date=11 April 2025 | quote=Close biosynthetic relatives of harmaline (harmine and tetrahydroharmine) are known components of plants of several other genera which have medical use but no reputation as hallucinogens [...] The effective dose range of harmaline in man is 70-100 mg i.v., or 300-400 mg orally. The initial effects are noted about one hour following oral administration and persist for about 6 hours [...] The indicators of physical toxicity are common and often severe. Paresthesias of hands, feet, or face are almost always present with the onset of effects, and are usually followed by the sensation of numbness. There can be isolated symptoms such as pressure in the head or chest, nausea and distressful vomiting, dizziness, and general malaise. Mydriasis and pressor effects are never seen. The anxiety and general discomfort encourages a withdrawal from social contact, and a quiet dark environment is preferred by most subjects. The modality most consistently affected by harmaline is the visual sense. There can be vivid images generated, often in the form of meaningful dream-like sequences, and frequently containing subject matter such as wild animals or jungle scenes. Other reported visual syntheses are limited to the generation of geometric patterns which are entertaining but not felt to be of any intrinsic significance.}}</ref><ref name="TiHKAL1997">{{cite web | title=Erowid Online Books : "TIHKAL" - #13 HARMALINE | website=www.erowid.org | url=http://www.erowid.org/library/books_online/tihkal/tihkal13.shtml | access-date=11 April 2025}}</ref> It is the partly [[hydrogenated]] form of [[harmine]]. It is a [[Monoamine oxidase inhibitor|reversible monoamine oxidase inhibitor]] (RIMA). It produces vivid [[dream]]-like [[Hallucination|visual effects]] and [[Side effect|physical discomfort]] at [[oral administration|oral]] doses of 300 to 400{{nbsp}}mg, often leading users to seek [[solitude]] in a quiet, dark environment.<ref name="Shulgin1977" /><ref name="TiHKAL1997" />
'''Harmaline''', also known as '''7-methoxyharmalan''' or as '''3,4-dihydro-7-methoxy-1-methyl-β-carboline''', is a [[fluorescent]] [[indole]] [[alkaloid]] from the group of [[harmala alkaloid]]s and [[substituted β-carboline|β-carboline]]s.<ref name="BrimblecombePinder1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | title = Hallucinogenic Agents | location = Bristol | pages = 98–144 | date = 1975 | publisher = Wright-Scientechnica | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1 | quote = [...] the apparent superiority of extracts of Banisteriopsis over the pure harmine prompted the suggestion (Hochstein and Paradies, 1957) that either harmaline or 1,2,3,4-tetrahydroharmine, or other as then unidentified constituents, were the psychoactive compounds. Naranjo (1967) has now confirmed their hallucinogenic activity in man together with that of 6-methoxyharmalan and 6-methoxytetrahydroharman. [...]}}</ref><ref name="Shulgin1977">{{cite journal | last=Shulgin | first=Alexander T. | title=Profiles of Psychedelic Drugs: 4. Harmaline | journal=Journal of Psychedelic Drugs | volume=9 | issue=1 | date=1977 | issn=0022-393X | doi=10.1080/02791072.1977.10472029 | pages=79–80 | url=https://www.tandfonline.com/doi/full/10.1080/02791072.1977.10472029 | access-date=11 April 2025 | quote=Close biosynthetic relatives of harmaline (harmine and tetrahydroharmine) are known components of plants of several other genera which have medical use but no reputation as hallucinogens [...] The effective dose range of harmaline in man is 70-100 mg i.v., or 300-400 mg orally. The initial effects are noted about one hour following oral administration and persist for about 6 hours [...] The indicators of physical toxicity are common and often severe. Paresthesias of hands, feet, or face are almost always present with the onset of effects, and are usually followed by the sensation of numbness. There can be isolated symptoms such as pressure in the head or chest, nausea and distressful vomiting, dizziness, and general malaise. Mydriasis and pressor effects are never seen. The anxiety and general discomfort encourages a withdrawal from social contact, and a quiet dark environment is preferred by most subjects. The modality most consistently affected by harmaline is the visual sense. There can be vivid images generated, often in the form of meaningful dream-like sequences, and frequently containing subject matter such as wild animals or jungle scenes. Other reported visual syntheses are limited to the generation of geometric patterns which are entertaining but not felt to be of any intrinsic significance.| url-access=subscription }}</ref><ref name="TiHKAL1997">{{cite web | title=Erowid Online Books : "TIHKAL" - #13 HARMALINE | website=www.erowid.org | url=http://www.erowid.org/library/books_online/tihkal/tihkal13.shtml | access-date=11 April 2025}}</ref> It is the partly [[hydrogenated]] form of [[harmine]]. It is a [[Monoamine oxidase inhibitor|reversible monoamine oxidase inhibitor]] (RIMA). It produces vivid [[dream]]-like [[Hallucination|visual effects]] and [[Side effect|physical discomfort]] at [[oral administration|oral]] doses of 300 to 400{{nbsp}}mg, often leading users to seek [[solitude]] in a quiet, dark environment.<ref name="Shulgin1977" /><ref name="TiHKAL1997" />


Plants containing harmaline are combined in [[ayahuasca]] to inhibit monoamine oxidase, allowing orally ingested [[N,N-Dimethyltryptamine|DMT]] to remain active in the brain and produce psychoactive effects. Harmala alkaloids, including harmaline, are psychoactive on their own in humans, with harmaline being particularly hallucinogenic, although other compounds such as [[harmine]] and [[tetrahydroharmine]]  have also been reported to produce hallucinogenic effects as well.
Plants containing harmaline are combined in [[ayahuasca]] to inhibit monoamine oxidase, allowing orally ingested [[N,N-Dimethyltryptamine|DMT]] to remain active in the brain and produce psychoactive effects. Harmala alkaloids, including harmaline, are psychoactive on their own in humans, with harmaline being particularly hallucinogenic, although other compounds such as [[harmine]] and [[tetrahydroharmine]]  have also been reported to produce hallucinogenic effects as well.

Latest revision as of 19:52, 23 June 2025

Template:Short description Template:Cs1 config Template:Drugbox

Harmaline, also known as 7-methoxyharmalan or as 3,4-dihydro-7-methoxy-1-methyl-β-carboline, is a fluorescent indole alkaloid from the group of harmala alkaloids and β-carbolines.[1][2][3] It is the partly hydrogenated form of harmine. It is a reversible monoamine oxidase inhibitor (RIMA). It produces vivid dream-like visual effects and physical discomfort at oral doses of 300 to 400Template:Nbspmg, often leading users to seek solitude in a quiet, dark environment.[2][3]

Plants containing harmaline are combined in ayahuasca to inhibit monoamine oxidase, allowing orally ingested DMT to remain active in the brain and produce psychoactive effects. Harmala alkaloids, including harmaline, are psychoactive on their own in humans, with harmaline being particularly hallucinogenic, although other compounds such as harmine and tetrahydroharmine have also been reported to produce hallucinogenic effects as well.

Harmaline exhibits weak affinity for 5-HT2A and 5-HT2C receptors, partially substitutes for the psychedelic DOM in rodents, inhibits acetylcholinesterase and histamine N-methyltransferase, and stimulates dopamine release at high doses.Script error: No such module "Unsubst".

Harmaline is present in Peganum harmala (Syrian rue). Syrian rue seeds contain about 3% harmala alkaloids by dry weight. Harmaline was first isolated from plants in 1841, its chemical structure identified in 1919, and it was first synthesized in 1927.

Use

Harmaline-containing plants and tryptamine-containing plants are used in ayahuasca brews. The inhibitory effects on monoamine oxidase allows dimethyltryptamine (DMT), the psychoactively prominent chemical in the mixture, to bypass the extensive first-pass metabolism it undergoes upon ingestion, allowing a psychologically active quantity of the chemical to exist in the brain for a perceivable period of time.[4]

Effects

The harmala alkaloids are psychoactive in humans.[5] According to Alexander Shulgin, harmaline is the only harmala alkaloid that has a reputation of being hallucinogenic.[2][6] However, other harmala alkaloids and β-carbolines, like harmine, tetrahydroharmine (THH), 6-methoxyharmalan, and 6-methoxytetrahydroharman, have also been reported to be hallucinogenic.[7]

Interactions

Harmaline is a reversible inhibitor of MAO-A (RIMA)".[8] This means that the risk of a hypertensive crisis, a dangerous high blood pressure crisis from eating tyramine-rich foods such as cheese, is likely lower with harmaline than with irreversible MAOIs such as phenelzine. Since harmaline is a RIMA, it could, in theory, induce both serotonin syndrome and hypertensive crises in combination with tyramine, serotonergics, catecholaminergics drugs or prodrugs.

Pharmacology

Harmaline activities
Target Affinity (Ki, nM)
5-HT1A >10,000 (rat/human)
5-HT1B >10,000
5-HT1D >10,000
5-HT1E ND
5-HT1F ND
5-HT2A 5,010–7,790 (Ki) (rat)
>20,000 (Template:Abbrlink)
>10,000 (Template:Abbrlink)
5-HT2B ND
5-HT2C 9,430 (rat)
5-HT3 >10,000
5-HT4 ND
5-HT5A >10,000
5-HT6 1,480
5-HT7 5,500
α1A >10,000
α1B >10,000
α1D ND
α2A 2,540
α2B 1,130
α2C 810
β1, β2 >10,000
β3 ND
D1–D5 >10,000 (human/rat)
H1–H4 ND
M1–M5 >10,000
I1 13,800
I2 22
σ1, σ2 ND
Template:Abbrlink ND
BDZ >10,000 (rat)
PCP >10,000 (rat)
Template:Abbrlink >10,000 (Ki)
Template:Abbrlink 3,260 (Ki)
Template:Abbrlink >10,000 (Ki) (bovine)
Template:Abbrlink 2.5–33 (IC50)
Template:Abbrlink 100,000 (IC50)
Template:Abbrlink 4,600 (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [9][10][11][12][7][13]

Harmaline shows weak but significant affinity for the serotonin 5-HT2A and 5-HT2C receptors (in the low micromolar range).[7][12] Harmaline and the psychedelic DOM partially substitute for each other in rodent drug discrimination tests.[14][7] Harmaline was much more effective in substituting for DOM than harman and harmine, which did not achieve significant generalization and produced behavioral disruption at higher doses.[14] On the other hand, harmaline and 6-methoxyharman were comparable in terms of DOM substitution.[14] Harmaline shows high affinity for the imidazoline I2 receptor (Ki = 22Template:NbspnM).[11]

Chemistry

File:Harmaline Harmine.jpg
Harmaline and harmine fluoresce under ultraviolet light. These three extractions indicate that the middle one has a higher concentration of the two compounds.

Harmaline, also known as 7-methoxyharmalan or 3,4-dihydro-7-methoxy-1-methyl-β-carboline, is a β-carboline and a cyclized tryptamine analogue of 6-methoxy-DMT.

It is fluorescent under ultraviolet light.

Natural occurrence

Various plants contain harmaline including Peganum harmala (Syrian rue) as well as the hallucinogenic beverage ayahuasca, which is traditionally brewed using Banisteriopsis caapi. Present at 3% by dry weight, the harmala alkaloids may be extracted from the Syrian rue seeds.[5]

History

Harmaline was first isolated from plants in 1841.[2] The chemical structure of harmaline was not correctly identified until 1919.[2] Harmaline was first synthesized in 1927.[2]

Society and culture

Legal status

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Australia

Harmala alkaloids are considered Schedule 9 prohibited substances under the Poisons Standard (October 2015).[15] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[15]

Canada

Harmaline and Harmalol are considered Schedule III controlled substances by the Controlled Drugs and Substances Act. Every person found to be in possession of a Schedule III drug is guilty of an indictable offence and liable to imprisonment for a term not exceeding three years; or for a first offence, guilty on summary conviction, to a fine not exceeding one thousand dollars or to imprisonment for a term not exceeding six months, or to both. Every person found to be trafficking a Schedule III drug is guilty of an indictable offence and liable to imprisonment for a term not exceeding ten years, or is guilty on summary conviction (first-time offenders) and liable to imprisonment for a term not exceeding eighteen months.[16]

See also

References

Template:Reflist

External links


Template:Psychedelics Template:Serotonin receptor modulators Template:Imidazoline receptor modulators Template:Acetylcholine metabolism and transport modulators Template:Monoamine metabolism modulators Script error: No such module "Navbox".

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