Phenoxyethylamine

Last updated
Phenoxyethylamine
Names
IUPAC name
2-phenoxyethanamine
Other names
2-Phenoxyethylamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C8H11NO/c9-6-7-10-8-4-2-1-3-5-8/h1-5H,6-7,9H2
    Key: IMLAIXAZMVDRGA-UHFFFAOYSA-N
  • C1=CC=C(C=C1)OCCN
Properties
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).

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

  1. 1 2 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.
  2. 1 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.
  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.


This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.