CAS号 192648-66-1 - methyl (3S,4R)-3-(2-acetyloxybenzoyl)oxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate

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: methyl (3S,4R)-3-(2-acetyloxybenzoyl)oxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate

英文名称：methyl (3S,4R)-3-(2-acetyloxybenzoyl)oxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate

CAS：
192648-66-1
分子式：C19H23NO6

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methyl (3S,4R)-3-(2-acet...简介

2′-Acetoxycocaine (ortho-acetoxy-cocaine) is a cocaine analog, with a quicker effect onset than cocaine. The acetoxy branch renders the molecule a QSAR of a 4-fold increase over cocaine in its binding potency for the dopamine transporter & a 35-fold enhanced affinity for the norepinephrine transporter. It also has a reduced selectivity for the serotonin transporter (though only due to its greater increase at NET & DAT binding being of such an order of magnitude more by comparison). In overall binding affinity (not uptake inhibition) it displaces ligands better across the board than cocaine in all monoamine categories. Salicylmethylecgonine would be an intermediate metabolite in vivo in humans (therefore affecting the overall effect profile of the administered 2′-acetoxy analog via its metabolic route; giving it nearly three times the affinity for DAT, after onset, and greaten the affinity that is would have for NET by a halve more than on upon initial exposure, after rapid deacetylation.) 2′-Acetoxycocaine has a closer to optimum LogP (a square value of 2) for blood–brain barrier penetration (cocaine being higher and logarithmically four times the optimal lipophilicity allowing too much of the compound to be dumped out directly into fatty tissue instead of reaching its target site) this would make it a prodrug to salicylmethylecgonine due to the latter having a less (and the ortho-acetoxy analog having a more) efficacious LogP than its cocaine parent.

methyl (3S,4R)-3-(2-acet...基本信息

中文名称	methyl (3S,4R)-3-(2-acetyloxybenzoyl)oxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate	英文名称	methyl (3S,4R)-3-(2-acetyloxybenzoyl)oxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate
中文别名	查看更多中文别名	英文别名	3-[(2'-acetoxybenzoyl)oxy]-[1R-(exo,exo)]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester; 2'-Acetoxycocaine; 查看更多英文别名
CAS号	192648-66-1	分子式	C19H23NO6
分子量	361.38900	精确质量	361.15300
PSA	82.14000	LOGP	1.73090