2′-Acetoxycocaine

2′-Acetoxycocaine

Names
IUPAC name (1R,2R,3S,5S)-Methyl 3-((2-acetoxybenzoyl)oxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Identifiers
CAS Registry Number	192648-66-1 Y
ChemSpider	8888946 Y
InChI InChI=1S/C19H23NO6/c1-11(21)25-15-7-5-4-6-13(15)18(22)26-16-10-12-8-9-14(20(12)2)17(16)19(23)24-3/h4-7,12,14,16-17H,8-10H2,1-3H3/t12-,14+,16-,17+/m0/s1 Y Key: BGTCUQCBSAMJBH-JSQNDZKTSA-N Y InChI=1/C19H23NO6/c1-11(21)25-15-7-5-4-6-13(15)18(22)26-16-10-12-8-9-14(20(12)2)17(16)19(23)24-3/h4-7,12,14,16-17H,8-10H2,1-3H3/t12-,14+,16-,17+/m0/s1 Key: BGTCUQCBSAMJBH-JSQNDZKTBL
Jmol-3D images	Image
PubChem	10713606
SMILES CN1C2C[C@H](OC(C3=C(OC(C)=O)C=CC=C3)=O)[C@H](C(OC)=O)C1CC2
Properties
Molecular formula	C19H23NO6
Molar mass	361.39 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

2′-Acetoxycocaine 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.^[1]

See also

• Salicylmethylecgonine

References

1. ↑ Seale, TW; Avor, K; Singh, S; Hall, N; Chan, HM; Basmadjian, GP (1997). "2'-Substitution of cocaine selectively enhances dopamine and norepinephrine transporter binding". Neuroreport 8 (16): 3571–5. doi:10.1097/00001756-199711100-00030. PMID 9427328.