Anhalinine

Anhalinine
Names
	Preferred IUPAC name 6,7,8-Trimethoxy-1,2,3,4-tetrahydroisoquinoline
	Other names O-Methylanhalamine; 6,7,8-Trimethoxy-THIQ; Anhalanine; Mescaline-CR
Identifiers
CAS Number	642-30-8;
3D model (JSmol)	Interactive image;
ChemSpider	167242;
PubChem CID	192723;
UNII	JZ4K38GMN6 ;
CompTox Dashboard (EPA)	DTXSID10982742 ;
	InChI InChI=1S/C12H17NO3/c1-14-10-6-8-4-5-13-7-9(8)11(15-2)12(10)16-3/h6,13H,4-5,7H2,1-3H3 Key: GOBKARNYNSWQFZ-UHFFFAOYSA-N; InChI=1/C12H17NO3/c1-14-10-6-8-4-5-13-7-9(8)11(15-2)12(10)16-3/h6,13H,4-5,7H2,1-3H3 Key: GOBKARNYNSWQFZ-UHFFFAOYAR;
	SMILES COC1=C(C(=C2CNCCC2=C1)OC)OC;
Properties
Chemical formula	C12H17NO3
Molar mass	223.272 g·mol−1
Melting point	60–61 °C (140–142 °F; 333–334 K)
Boiling point	144–145 °C (291–293 °F; 417–418 K) at 0.1 Torr
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Anhalinine, also known as O-methylanhalamine or mescaline-CR, is a tetrahydroisoquinoline alkaloid found in Lophophora williamsii (peyote) and other cacti. It is structurally related to mescaline and is a cyclized phenethylamine analogue of mescaline. Anhalinine is also pharmacologically active, but is only a minor constituent of peyote and is unlikely to contribute to its effects.

Simple isoquinoline alkaloids of mescaline-containing cacti like anhalinine have received relatively little investigation. Arthur Heffter found many of them to produce no effects similar to those of mescaline. However, some of them have been found to produce convulsions in animals at high doses. Anhalinine specifically has been described as having "stimulant" properties due to inhibiting cholinergic neurotransmission. Alexander Shulgin tried anhalinine at small doses of 0.5 to 4.3 mg but experienced no effects.

Anhalinine has been found to act as a low-potency inverse agonist of the serotonin 5-HT₇ receptor, with an EC₅₀Tooltip half-maximal effective concentration of 2,722 nM and an E_maxTooltip half-maximal effective concentration of –85%. This was much less potent in terms of this action than certain other tetrahydroisoquinolines like pellotine and anhalidine. Serotonin 5-HT₇ receptor inverse agonism might be involved in the sedative and hypnotic effects of certain peyote alkaloids like pellotine and anhalonidine.

Anhalinine was first isolated from peyote by Ernst Späth in 1935. Shulgin bioassayed it in 1963.