InChI=1/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12?,13?,14-,15+/m0/s1

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Inherent Properties, Identifiers and References

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ChemSpider ID:	5557
Empirical Formula:	C₁₇H₂₁NO₄
Molecular Weight:	303.3529
Nominal Mass:	303 Da
Average Mass:	303.3529 Da
Monoisotopic Mass:	303.147058 Da

Systematic Name:

methyl (2R,3S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

SMILES:

O=C(O[C@H]1CC2N(C)C([C@H]1C(=O)OC)CC2)c3ccccc3

InChI:

InChI=1/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12?,13?,14-,15+/m0/s1

InChIKey:

ZPUCINDJVBIVPJ-PFSRBDOWBP

Original Reference(s)

Data Source	External ID(s)
ChemIDplus	000050362
Christopher Data	N/A
DiscoveryGate	5760
DrugBank	5760, APRD00080
NIAID	154465
PubChem	5760

Disclaimer (Details...)

Supplemental Information

Links & References

GC of cocaine on Phenomenex Zebron ZB-1 with MS detection

Names and Synonyms

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

cocaine[Wiki]

(+)-Cocaine

(S)-(+)-Cocaine

50-36-2[RN]

8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, (2R,3S)-

Cocaine, l-

Benzoylethylecgonine

Benzoylmethylecgonine[Wiki]

beta-Cocain

Cocain[Wiki]

Cocaina

Cocaine free base

Cocaine-M

Coke

Corine

crazy crack

Delcaine

Depsococaine

Dextrocaine

d-Pseudococaine

Ecgonine, Methyl Ester, Benzoate

Eritroxilina

Erytroxylin

Heaven[Wiki]

Isococain

Isococaine

Kokain

Kokan[Wiki]

Kokayeen

l-Cocain

L-Cocaine

Methyl 3beta-hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylate benzoate (ester)

Methyl Benzoylecgonine

Neurocaine

(1R,2R,3S,5S)-2-Methoxycarbonyltropan-3-yl benzoate

1-alpha-H,5-alpha-H-Tropane-2-beta-carboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate

1-Cocaine

200-032-7[EINECS]

2beta-Carbomethoxy-3beta-benzoxytropane

2-beta-Carbomethoxy-3-beta-benzoxytropane

2-beta-Tropanecarboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate (ester)

3-(Benzoyloxy)-8-methyl-8-azabicyclo-(3.2.1)octane-2-carboxylic acid methyl ether

337376-15-5[RN]

3-Tropanylbenzoate-2-carboxylic acid methyl ester

8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, (1R-(exo,exo))-

Cocaine [BAN]

Ecgonine, methyl ester, benzoate (ester)

Methyl 3-beta-hydroxy-1-alpha-H,5-alpha-H-tropane-2-beta-carboxylate benzoate (ester)

Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

AIDS154465

AIDS-154465

DEA No. 9041

HSDB 6469

Predicted Properties

LogP:	ACD/LogP: 3.08 XLogP: 2.30	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	0.13	ACD/LogD (pH 7.4):	1.51
ACD/BCF (pH 5.5):	1	ACD/BCF (pH 7.4):	3.5
ACD/KOC (pH 5.5):	1.28	ACD/KOC (pH 7.4):	30.61
#H bond acceptors:	5	#H bond donors:	0
#Freely Rotating Bonds:	5	Polar Surface Area:	55.84 Å²
Index of Refraction:	1.567	Molar Refractivity:	81.1 cm³
Molar Volume:	248 cm³	Polarizability:	32.15 10^-24cm³
Surface Tension:	48.4 dyne/cm	Density:	1.22 g/cm³
Flash Point:	192.8 °C	Enthalpy of Vaporization:	64.53 kJ/mol
Boiling Point:	395.2 °C at 760 mmHg	Vapour Pressure:	1.87E-06 mmHg at 25°C

SimBioSys LASSO

Descriptors: 0, 0, 0, 0, 0, 0, 0, 5, 2, 0, 0, 0, 7, 5, 9, 0, 6, 4, 2, 0, 0, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Other Enzymes	AChE, acetylcholinesterase	1eve	0.94
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Serine Proteases	Thrombin	1ba8	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Kinases	HSP90, human heat shock protein 90	1uy6	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00

Spectra

Type: Infrared