Carnegine

Carnegine
Names
	IUPAC name 6,7-dimethoxy-1,2-dimethyl-3,4-dihydro-1H-isoquinoline
	Other names Pectenine; DMMM-4; 6,7-Dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline; 6,7-Dimethoxy-1,2-dimethyl-THIQ
Identifiers
CAS Number	490-53-9 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL5272718;
ChemSpider	21227;
KEGG	C09375;
PubChem CID	22646;
UNII	EOW70A27WK;
CompTox Dashboard (EPA)	DTXSID30871689 ;
	InChI InChI=1S/C13H19NO2/c1-9-11-8-13(16-4)12(15-3)7-10(11)5-6-14(9)2/h7-9H,5-6H2,1-4H3 Key: HRSIPKSSEVRSPG-UHFFFAOYSA-N;
	SMILES CC1C2=CC(=C(C=C2CCN1C)OC)OC;
Properties
Chemical formula	C13H19NO2
Molar mass	221.300 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Carnegine, also known as pectenine, DMMM-4, or 6,7-dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline, is a tetrahydroisoquinoline and cyclized phenethylamine alkaloid found in the cacti species Carnegiea gigantea and Pachycereus pringlei.^[1]^[2]^[3]^[4]^[5]^[6]^[7]

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It is known to be pharmacologically active, including acting as a relatively potent monoamine oxidase inhibitor (MAOI), specifically of monoamine oxidase A (MAO-A) (K_i = 2 μM for the (R)-enantiomer) but not of monoamine oxidase B (MAO-B), producing strychnine-like convulsions in animals, and having other actions and effects.^[2]^[3]^[8] Carnegine and similar alkaloids might potentiate the effects of mescaline and related compounds like N-methylmescaline via monoamine oxidase inhibition.^[3]^[2]^[9]

The compound was first isolated in 1901 and was first synthesized in 1929.^[4]^[3]

See also