Phenoxyethylamine

Phenoxyethylamine
Names
	IUPAC name 2-phenoxyethanamine
	Other names 2-Phenoxyethylamine
Identifiers
CAS Number	1758-46-9;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL217680;
ChemSpider	14886;
PubChem CID	15651;
UNII	8DGQ1B38R5;
	SMILES C1=CC=C(C=C1)OCCN;
Properties
Chemical formula	C8H11NO
Molar mass	137.182 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

Phenoxyethylamine, also known as 2-phenoxyethylamine, is a chemical compound related to phenethylamine (2-phenylethylamine). It is a parent compound of several psychedelic-related drugs including 3,4,5-trimethoxyphenoxyethylamine, CT-4719 (2,4-dichloro-5-methoxyphenoxyethylamine),^[1] CT-5126,^[1] and ORG-37684. It is also a parent compound of other drugs like the α-adrenergic receptor antagonist phenoxybenzamine,^[2] the α₂-adrenergic receptor modulators lofexidine, allyphenyline, and cyclomethyline,^[3] the β-adrenergic receptor agonists dextrofemine and isoxsuprine, the beta blocker carvedilol,^[2] the antihistamine phenyltoloxamine, the sodium channel blocker mexiletine, and the coronary vasodilator fenalcomine, among others.

References

^ ^a ^b Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144 (75–76). ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. Addition of an oxygen atom to give the phenoxyethylamines was attended with more success. Several compounds were hyperthermic in animals and produced behavioural syndromes characteristic of hallucinogenic drugs (Julia and de Rosnay, 1969, 1970); 2,4 dichloro-5-methoxyphenoxyethylamine (3.62) was twice as potent as mescaline in producing changes in the E.E.G. and E.CoG. of cats (Rougeul, 1969; Rougeul and Verdaux, 1972). Such LSD-like effects were not apparent, however, with the cyclic analogue (3.63) or 3,5-dichloro-2,6-dimethoxyphenoxyethylamine (3.64), emphasizing the importance of the free ethylamine side-chain and the 4-substituent. It will be interesting if such results can be extended to the phenoxyisopropylamines analogous to the amphetamines.
^ ^a ^b Nichols AJ, Sulpizio AC, Ashton DJ, Hieble JP, Ruffolo RR (1989). "The interaction of the enantiomers of carvedilol with alpha 1- and beta 1-adrenoceptors". Chirality. 1 (4): 265–270. doi:10.1002/chir.530010404. PMID 2577144.
^ Del Bello F, Diamanti E, Giannella M, Mammoli V, Marchioro C, Mattioli L, Titomanlio F, Piergentili A, Quaglia W, Benedetti G, Varrone M, Pigini M (July 2012). "Low Doses of Allyphenyline and Cyclomethyline, Effective against Morphine Dependence, Elicit an Antidepressant-like Effect". ACS Med Chem Lett. 3 (7): 535–539. doi:10.1021/ml300064v. PMC 4025786. PMID 24900506.

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[BrimblecombePinder1975-1] Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144 (75–76). ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. Addition of an oxygen atom to give the phenoxyethylamines was attended with more success. Several compounds were hyperthermic in animals and produced behavioural syndromes characteristic of hallucinogenic drugs (Julia and de Rosnay, 1969, 1970); 2,4 dichloro-5-methoxyphenoxyethylamine (3.62) was twice as potent as mescaline in producing changes in the E.E.G. and E.CoG. of cats (Rougeul, 1969; Rougeul and Verdaux, 1972). Such LSD-like effects were not apparent, however, with the cyclic analogue (3.63) or 3,5-dichloro-2,6-dimethoxyphenoxyethylamine (3.64), emphasizing the importance of the free ethylamine side-chain and the 4-substituent. It will be interesting if such results can be extended to the phenoxyisopropylamines analogous to the amphetamines.

[NicholsSulpizioAshton1989-2] Nichols AJ, Sulpizio AC, Ashton DJ, Hieble JP, Ruffolo RR (1989). "The interaction of the enantiomers of carvedilol with alpha 1- and beta 1-adrenoceptors". Chirality. 1 (4): 265–270. doi:10.1002/chir.530010404. PMID 2577144.

[DelBelloDiamantiGianella2012-3] Del Bello F, Diamanti E, Giannella M, Mammoli V, Marchioro C, Mattioli L, Titomanlio F, Piergentili A, Quaglia W, Benedetti G, Varrone M, Pigini M (July 2012). "Low Doses of Allyphenyline and Cyclomethyline, Effective against Morphine Dependence, Elicit an Antidepressant-like Effect". ACS Med Chem Lett. 3 (7): 535–539. doi:10.1021/ml300064v. PMC 4025786. PMID 24900506.

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