Harmaline

Harmaline
Clinical data
Dependence; liability	N/A
Routes of; administration	Ingestion
Legal status
Legal status	AU: S9 (Prohibited substance); CA: Schedule III;
Identifiers
	IUPAC name 7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole;
CAS Number	304-21-2 ;
PubChem CID	5280951;
ChemSpider	10211258 ;
UNII	CN58I4TOET;
KEGG	C06536 ;
ChEBI	CHEBI:28172 ;
ChEMBL	ChEMBL340807 ;
CompTox Dashboard (EPA)	DTXSID8041038 ;
ECHA InfoCard	100.005.594
Chemical and physical data
Formula	C13H14N2O
Molar mass	214.268 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	232–234 °C (450–453 °F)
	SMILES COc3ccc2c1CCN=C(C)c1[nH]c2c3;
	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 ; Key:RERZNCLIYCABFS-UHFFFAOYSA-N ;
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Harmaline is a fluorescent indole alkaloid from the group of harmala alkaloids and beta-carbolines. It is the partly hydrogenated form of harmine.

Clinical data


Dependence liability	N/A
Routes of administration	Ingestion
Legal status
Legal status	AU: S9 (Prohibited substance) 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
KEGG	C06536^Y
ChEBI	CHEBI:28172^N
ChEMBL	ChEMBL340807^Y
CompTox Dashboard (EPA)	DTXSID8041038
ECHA InfoCard	100.005.594
Chemical and physical data
Formula	C₁₃H₁₄N₂O
Molar mass	214.268 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	232–234 °C (450–453 °F)
SMILES COc3ccc2c1CCN=C(C)c1[nH]c2c3
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?) (verify)