Back حرملين Arabic هارمالین AZB Harmalin German Harmalina Spanish هارمالین Persian Harmaliini Finnish Harmaline French Armalina Italian ハルマリン Japanese Harmalina Polish
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| Dependence liability | N/A |
| Routes of administration | Ingestion |
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| ECHA InfoCard | 100.005.594 |
| Chemical and physical data | |
| Formula | C13H14N2O |
| Molar mass | 214.268 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 232–234 °C (450–453 °F) |
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Harmaline is a fluorescent indole alkaloid from the group of harmala alkaloids and β-carbolines.[1][2] It is the partly hydrogenated form of harmine. The drug is a monoamine oxidase inhibitor (MAOI) and mild psychedelic with pronounced physical side effects.[1][2]
- ^ a b Shulgin AT (1977). "Profiles of Psychedelic Drugs: 4. Harmaline". Journal of Psychedelic Drugs. 9 (1): 79–80. doi:10.1080/02791072.1977.10472029. ISSN 0022-393X. Retrieved 11 April 2025.
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.
- ^ a b "Erowid Online Books : "TIHKAL" - #13 HARMALINE". www.erowid.org. Retrieved 11 April 2025.