Enadoline

Enadoline
Clinical data
ATC code	none;
Identifiers
	IUPAC name 2-(1-Benzofuran-4-yl)-N-methyl-N-[(5R,7S,8S)-7-pyrrolidin-1-yl-1-oxaspiro[4.5]decan-8-yl]acetamide;
CAS Number	124378-77-4 ;
PubChem CID	60768;
IUPHAR/BPS	1646;
ChemSpider	54765 ;
UNII	KJL283326C;
ChEMBL	ChEMBL318859 ;
CompTox Dashboard (EPA)	DTXSID4047258 ;
Chemical and physical data
Formula	C24H32N2O3
Molar mass	396.52 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(Cc1cccc2occc12)N(C)C1CCC2(CCCO2)CC1N1CCCC1;
	InChI InChI=1S/C24H32N2O3/c1-25(23(27)16-18-6-4-7-22-19(18)9-15-28-22)20-8-11-24(10-5-14-29-24)17-21(20)26-12-2-3-13-26/h4,6-7,9,15,20-21H,2-3,5,8,10-14,16-17H2,1H3/t20-,21-,24-/m0/s1 ; Key:JMBYBVLCYODBJQ-HFMPRLQTSA-N ;
	(verify)

Enadoline is a drug which acts as a highly selective κ-opioid agonist.

In human studies, it produced visual distortions and feelings of dissociation, reminiscent of the effects of salvinorin A.^[1]

It was studied as a potential analgesic, but abandoned because of the dose-limiting effects of dysphoria, which could be expected from a κ-opioid agonist. There was mention of its potential in treating comatose head injury or stroke victims, where that type of side effect would be immaterial.^[2]

Potency

When enadoline was first reported in 1990, it was "the most potent κ-selective analgesic ever reported ... 25 times more potent than morphine and 17 times more potent than U-62066".^[3]

References

^ Walsh SL, Strain EC, Abreu ME, Bigelow GE (2001). "Enadoline, a selective kappa opioid agonist: comparison with butorphanol and hydromorphone in humans". Psychopharmacology (Berl.). 157 (2): 151–62. doi:10.1007/s002130100788. PMID 11594439.
^ Barber A, Gottschlich R (1997). "Novel developments with selective, non-peptidic kappa-opioid receptor agonists". Expert Opin Investig Drugs. 6 (10): 1351–68. doi:10.1517/13543784.6.10.1351. PMID 15989506.
^ Halfpenny, Paul R.; Horwell, David C.; Hughes, John; Hunter, John C.; Rees, David C. (1990). "Highly selective .kappa.-opioid analgesics. 3. Synthesis and structure-activity relationships of novel N-[2-(1-pyrrolidinyl)-4- or -5-substituted cyclohexyl]arylacetamide derivatives". Journal of Medicinal Chemistry. 33 (1): 286–91. doi:10.1021/jm00163a047. PMID 2153208.

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[pmid11594439-1] Walsh SL, Strain EC, Abreu ME, Bigelow GE (2001). "Enadoline, a selective kappa opioid agonist: comparison with butorphanol and hydromorphone in humans". Psychopharmacology (Berl.). 157 (2): 151–62. doi:10.1007/s002130100788. PMID 11594439.

[pmid15989506-2] Barber A, Gottschlich R (1997). "Novel developments with selective, non-peptidic kappa-opioid receptor agonists". Expert Opin Investig Drugs. 6 (10): 1351–68. doi:10.1517/13543784.6.10.1351. PMID 15989506.

[halfpenny-3] Halfpenny, Paul R.; Horwell, David C.; Hughes, John; Hunter, John C.; Rees, David C. (1990). "Highly selective .kappa.-opioid analgesics. 3. Synthesis and structure-activity relationships of novel N-[2-(1-pyrrolidinyl)-4- or -5-substituted cyclohexyl]arylacetamide derivatives". Journal of Medicinal Chemistry. 33 (1): 286–91. doi:10.1021/jm00163a047. PMID 2153208.

[1]

[2]

[3]

Potency

See also

References