Harmaline

Harmaline
Clinical data


Dependence liability	N/A
Routes of administration	Ingestion
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule III
Identifiers
IUPAC name 7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
CAS Number	304-21-2^Y
PubChem (CID)	5280951
ChemSpider	10211258^Y
UNII	CN58I4TOET^Y
KEGG	C06536^Y
ChEBI	CHEBI:28172^N
ChEMBL	CHEMBL340807^Y
ECHA InfoCard	100.005.594
Chemical and physical data
Formula	C₁₃H₁₄N₂O
Molar mass	214.263 g/mol
3D model (Jmol)	Interactive image
Melting point	232–234 °C (450–453 °F)
SMILES C\C2=N\CCc1c3ccc(OC)cc3nc12
InChI InChI=1S/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,15H,5-6H2,1-2H3^Y Key:RERZNCLIYCABFS-UHFFFAOYSA-N^Y
^NY (what is this?)

Harmaline is a fluorescent psychoactive indole alkaloid from the group of harmala alkaloids and beta-carbolines. It is the partially hydrogenated form of harmine.

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.

Harmaline is a central nervous system stimulant and a "reversible inhibitor of MAO-A (RIMA)". 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.

The harmala alkaloids are psychoactive in humans. Harmaline is shown to act as an acetylcholinesterase inhibitor. Harmaline also stimulates striatal dopamine release in rats at very high dose levels. Since harmaline is a reversible inhibitor of monoamine oxidase A, it could, in theory, induce both serotonin syndrome and hypertensive crises in combination with tyramine, serotonergics, catecholaminergics drugs or prodrugs. Harmaline containing plants and tryptamine containing plants are used in ayahausca brews. The inhibitory effects on monoamine oxidase allows dimethyltryptamine (DMT), the psychologically 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. Harmaline forces the anabolic metabolism of serotonin into normelatonin or n-acetylserotonin, and then to melatonin, the body's principle sleep-regulating hormone and a powerful antioxidant.

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Wikipedia