3-Monoacetylmorphine

3-Monoacetylmorphine
Clinical data
Other names	3-Acetylmorphine, O(3)-monoacetylmorphine
Routes of; administration	Intravenous
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); UK: Class A; US: Schedule I;
Identifiers
	IUPAC name 3-acetyl-6-hydroxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan;
CAS Number	5140-28-3 ;
PubChem CID	5462504;
ChemSpider	4575431 ;
UNII	9N7243EY5T;
CompTox Dashboard (EPA)	DTXSID30183774 ;
ECHA InfoCard	100.208.392
Chemical and physical data
Formula	C19H21NO4
Molar mass	327.380 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)OC1=C2C3=C(C[C@@H]4[C@H]5[C@]3(CCN4C)[C@@H](O2)[C@H](C=C5)O)C=C1;
	InChI InChI=1S/C19H21NO4/c1-10(21)23-15-6-3-11-9-13-12-4-5-14(22)18-19(12,7-8-20(13)2)16(11)17(15)24-18/h3-6,12-14,18,22H,7-9H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1 ; Key:GMLREHXYJDLZOU-LEPYJNQMSA-N ;
	(verify)

3-Monoacetylmorphine (3-MAM) or 3-acetylmorphine is a less active metabolite of heroin (diacetylmorphine), the other two being morphine and more active 6-monoacetylmorphine (6-MAM).

Because of the acetyl-group in 3-position, 3-MAM has relatively weak affinity to μ-opioid receptors.

As 3-O-acetylmorphine-6-O-sulfate (C₁₉H₂₃NO₇S), where 6-OH is changed to 6-O-SO₃, it can act as a potent, centrally acting morphine derivative and has important analgesic properties.^[1]^[2]^[3]

3-MAM-6-Sulfate (M3A6S)

Acetyl groups of heroin. In 3-MAM lower group is changed to hydrogen making hydroxyl-group in 6-position.

References

↑ Houdi AA, Kottayil S, Crooks PA, Butterfield DA (March 1996). "3-O-acetylmorphine-6-O-sulfate: a potent, centrally acting morphine derivative". Pharmacology, Biochemistry, and Behavior. 53 (3): 665–671. doi:10.1016/0091-3057(95)02067-5. PMID 8866970. S2CID 14870642.
↑ Crooks PA, Kottayil SG, Al-Ghananeem AM, Byrn SR, Butterfield DA (August 2006). "Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners". Bioorganic & Medicinal Chemistry Letters. 16 (16): 4291–4295. doi:10.1016/j.bmcl.2006.05.060. PMID 16777416.
↑ Brock CP, Kottayil S, Butterfield DA, Crooks PA (January 1996). "A Dihydromorphine-6-O-sulfate". Acta Crystallographica Section C. 52 (1): 122–5. doi:10.1107/S0108270195010250.

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[1] Houdi AA, Kottayil S, Crooks PA, Butterfield DA (March 1996). "3-O-acetylmorphine-6-O-sulfate: a potent, centrally acting morphine derivative". Pharmacology, Biochemistry, and Behavior. 53 (3): 665–671. doi:10.1016/0091-3057(95)02067-5. PMID 8866970. S2CID 14870642.

[2] Crooks PA, Kottayil SG, Al-Ghananeem AM, Byrn SR, Butterfield DA (August 2006). "Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners". Bioorganic & Medicinal Chemistry Letters. 16 (16): 4291–4295. doi:10.1016/j.bmcl.2006.05.060. PMID 16777416.

[3] Brock CP, Kottayil S, Butterfield DA, Crooks PA (January 1996). "A Dihydromorphine-6-O-sulfate". Acta Crystallographica Section C. 52 (1): 122–5. doi:10.1107/S0108270195010250.

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