Harmine notes

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 MAO 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 ataxia 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.