Other Names

Harmaline: 4,9-dihydro-7-methoxy-1-methyl-3Hpyriol[

3,4-b] indole, harmalin, harmalolmethylester,

harmidin, harmidin, 3,4-dihydroharmin

Harmine: banisterin, banisterine, harmin,

7-methoxy-1-methyl-f3-carboline, telepathin, telepathine,

yageine

Empirical formula: C13H14N20 (harmaline),

C13H12N20 (harmine)

Substance type: f3-carbolines, harmala alkaloids

(indole alkaloids)

Harmaline and harmine are found in Banisteriopsis

caapi and Peganum harmala (Beringer

1928; Beringer 1929; Chen and Chen 1939).

Harmine also occurs in numerous other plants

(see ayahuasca analogs). Harmaline and harmine

not only are strong MAOMonoamine Oxidase, an enzyme that catalyses the metabolism of many drugs (e.g., DMT, dopamine and serotonin). inhibitors (Pletscher et

al. 1959; cf. f3-carbolines) but also have antibacterial

properties (Ahmad et al. 1992). Harmine

was an early treatment for Parkinson's disea~e

(Halpern 1930b):

Harmine lessens the exaggerated excitability of

the parasympathetic system in Parkinson's

patients, increases the low excitability of the

sympathetic system, also promotes the excitability

of the vestibular apparatus, and puts the

patient in a state of euphoria, helping them to

better accept their affliction. (Roth et al. 1994,

548*)

In the 1960s, the Chilean psychiatrist Claudio

Naranjo (1969*) introduced harmaline and

harmine to psychotherapy as "fantasy-increasing

drugs" (cf. ibogaine). The extent to which these

substances are psychoactive is questionable. To investigate the supposed "psychedelic" effect of

harmine,

Maurer (together with Lamparter and

Dittrich) tested the hypothesis that harmine is

a hallucinogen in 11 self-experiments with a

sublingual dosage between 25 and 750 mg.

Contrary to expectations, however, harmine

did not prove to be a substance that exhibited

many similarities to classic hallucinogens such

as mescaline or psilocybin. Maurer

characterized the state that harmine induced

as more of a retreat from one's surroundings

and as a pleasant relaxation with a mildly

reduced ability to concentrate. Short-term and

elementary optic hallucinatory phenomena

were observed only to the degree that they

would otherwise also appear naturally during

reduced contact with one's surroundings.

With dosages above 300 mg, such undesirable

vegetative and neurological symptoms as

dizziness, nausea, and ataxiaLoss of motor coordination became more

apparent, precluding any increase in dosage

above 750 mg. (Leuner and Schlichting 1986,

170*)

Most experimenters have called into question

the reports that Naranjo (1979*) published from

his psychotherapeutic practice. It may be that he

administered ayahuasca, and not any pure substances,

to his patients.

Today, harmaline and harmine are primarily

used in the production of pharmahuasca (ayahuasca

analogs).
Commercial Forms and Regulations

Both substances are available through chemical

suppliers. They may be purchased without restriction

and are not subject to any legal regulations

(Ott 1993,438*).

Literature

See also the entries for Banisteriopsis caapi, Peganum

harmala, ayahuasca, ayahuasca analogs,

~-carbolines,and indole alkaloids.

Ahmad, Aqeel, Kursheed Ali Khan, Sabiha Sultana,

Bina S. Siddiqui, Sabira Begum, Shaheen Faizi,

and Salimuzzaman Siddiqui. 1992. Study of in

vitro antimicrobial activity of harmine,

harmaline and their derivatives. Journal of

Ethnopharmacology 35:289-94.

Beringer, Kurt. 1928. "Ober ein neues, auf das extrapyramidal-

motorische System wirkendes

Alkaloid (Banisterin). Der Nervenarzt 1:265-75.

---.1929. Zur Banisterin und Harminfrage. Der

Nervenarzt 2:545-49.

Beringer, Kurt, and K. Willmanns. 1929. Zur

Harmin-Banisterin Frage. Deutsche medizinische

Wochenschrift 55:2081-86.

Chen, A. 1., and K. K. Chen. 1939. Harmine: The

alkaloid of caapi. Quarterly Journal ofPharmacy

and Pharmacology 12:30-38.

Halpern, 1. 1930a. "Ober die Harminwirkung im

Selbstsversuch. Deutsche medizinische

Wochenschrift 56:1252-54.

---. 1930b. Der Wirkungsmechanismus des

Harmins und die Pathophysiologie der

Parkinsonschen Krankheit. Deutsche medizinische

Wochenschrift 56:651-55.

Manske, R. H. E, et al. 1927. Harmine and

harmaline: Part IX: A synthesis of harmaline.

Journal ofthe Chemical Society (Organic) (1927):

1-15.

Pennes, H. H., and P. H. Hoch. 1957.

Psychotomimetics, clinical and theoretical

considerations: Harmine, WIN-2299 and nalline.

American Journal for Psychiatry 113:887-92.

Pletscher, A., et al. 1959. "Ober die pharmakologische

Beeinflussung des Zentralnervensystems durch

kurzwirkende Monoaminooxydasehemmer aus

der Gruppe der Harmala-Alkaloide. Helvetica

Physiologica et Pharmacologica Acta 17:202-14.

Spath, E., and F. Lederer. 1930. Synthese der Harma

Alkaloide: Harmalin, Harmin und Harman.

Berichte der deutschen chemischen Gesellschaft

63:120-25.

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