Cocaine

Details

• Internal ID: 47b6bcf9-aa87-47e6-ba46-c5fd3f2e65a7
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Benzoic acid esters
• IUPAC Name: methyl (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• SMILES (Canonical): CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC
• SMILES (Isomeric): CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)OC
• InChI: InChI=1S/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
• InChI Key: ZPUCINDJVBIVPJ-LJISPDSOSA-N
• Popularity: 64,847 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.35 g/mol
• Exact Mass: 303.14705815 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• Benzoylmethylecgonine
• Neurocaine
• Kokain
• Cocain
• L-Cocaine
• Cocaina
• beta-Cocain
• (-)-Cocaine
• cocainum
• Methyl Benzoylecgonine
• Coke
• l-Cocain
• Eritroxilina
• Erytroxylin
• Bernies
• Kokayeen
• Burese
• Corine
• Kokan
• Dama blanca
• Pimp's drug
• 1-Cocaine
• White girl or lady
• Star-spangled powder
• Leaf
• Snow
• Nose candy
• Cocaine free base
• Cocaine, l-
• C Carrie
• 50-36-2
• Blow [Street Name]
• Girl [Street Name]
• Lady [Street Name]
• Rock [Street Name]
• Toot [Street Name]
• Cecil [Street Name]
• Flake [Street Name]
• (r)-(-)-cocaine
• Bernice [Street Name]
• CHEBI:27958
• HSDB 6469
• Ecgonine, methyl ester, benzoate (ester)
• Gold dust [Street Name]
• 2-beta-Carbomethoxy-3-beta-benzoxytropane
• Happy dust [Street Name]
• UNII-I5Y540LHVR
• I5Y540LHVR
• Bernice
• Cholly
• Cecil
• Girl
• 2beta-Carbomethoxy-3beta-benzoxytropane
• Happy dust
• Gold dust
• IDS-NC-004
• Star dust
• 3-Tropanylbenzoate-2-carboxylic acid methyl ester
• Cholly [Street Name]
• Cocaine [USP:BAN]
• (1R,2R,3S,5S)-2-Methoxycarbonyltropan-3-yl benzoate
• 2-beta-Tropanecarboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate (ester)
• EINECS 200-032-7
• RX0041
• Star dust [Street Name]
• Green gold [Street Name]
• RX-0041
• Happy trails [Street Name]
• Methyl 3beta-hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylate benzoate (ester)
• Jam
• DTXSID2038443
• Crack cocaine
• 2-Methyl-3beta-hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylate benzoate (ester)
• 3beta-Hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylic acid methyl ester benzoate
• 1-alpha-H,5-alpha-H-Tropane-2-beta-carboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate
• 3-(Benzoyloxy)-8-methyl-8-azabicyclo-(3.2.1)octane-2-carboxylic acid methyl ether
• methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• Methyl 3-beta-hydroxy-1-alpha-H,5-alpha-H-tropane-2-beta-carboxylate benzoate (ester)
• Blow (Street Name)
• Girl (Street Name)
• Lady (Street Name)
• Rock (Street Name)
• Toot (Street Name)
• Ecgonine methyl ester benzoate (ester)
• Cecil (Street Name)
• COC
• Flake (Street Name)
• (1R,2R,3S,5S)-2-(methoxycarbonyl)tropan-3-yl benzoate
• Cholly (Street Name)
• Cocaine (USP:BAN)
• Bernice (Street Name)
• Crack
• Flake
• Blow
• Lady
• Toot
• Happy trails
• COCAINE (MART.)
• COCAINE [MART.]
• Green gold
• Gold dust (Street Name)
• Star dust (Street Name)
• 3beta-Hydroxy-2beta-tropanecarboxylic acid methyl ester benzoate (ester)
• 8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, (1R-(exo,exo))-
• Green gold (Street Name)
• Happy dust (Street Name)
• Happy trails (Street Name)
• methyl [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• C" Carrie
• COCAINE (USP MONOGRAPH)
• COCAINE [USP MONOGRAPH]
• Sleighride
• Badrock
• Bazooka
• Blizzard
• Cabello
• Charlie
• Cocktail
• Goofball
• Moonrocks
• Blast
• Candy
• Caviar
• Freeze
• Heaven
• Snort
• Trails
• Coca
• Cola
• Hell
• Toke
• Yeyo
• beta-Cocaine
• Bouncing Powder
• Chicken Scratch
• Happy powder
• Florida Snow
• Sweet Stuff
• Prime Time
• Foo Foo
• Kibbles n' Bits
• Snow (birds)
• G-Rock
• [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester
• METHYL (1R,2R,3S,5S)-3-(BENZOYLOXY)-8-METHYL-8-AZABICYCLO(3.2.1) OCTANE-2-CARBOXYLATE
• methyl (1R,2R,3S,5S)-8-methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylate
• Ecgonine methyl ester benzoate
• methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylate
• methyl (1R-(exo,exo))-3-(benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylate
• (1R-(exo,exo))-3-(benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester
• Cocaine (-)
• 1i7z
• COCAINE [VANDF]
• COCAINUM [HPUS]
• COCAINE [HSDB]
• COCAINE [MI]
• COCAINE [WHO-DD]
• Epitope ID:158626
• SCHEMBL21930
• CHEMBL370805
• GTPL2286
• DEA No. 9041
• BDBM22418
• Cocaine, 1mg/ml in Acetonitrile
• 1q72
• ZPUCINDJVBIVPJ-LJISPDSOSA-N
• DTXCID501030562
• Cocaine 0.1 mg/ml in Acetonitrile
• Cocaine 1.0 mg/ml in Acetonitrile
• AKOS015965554
• DB00907
• C01416
• Q41576
• [1R-(exo,exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid
• 3.BETA.-HYDROXY-2.BETA.-TROPANECARBOXYLIC ACID METHYL ESTER BENZOATE (ESTER)
• METHYL 3B-HYDROXY-1.ALPHA.H,5.ALPHA.H-TROPANE-2.BETA.-CARBOXYLATE BENZOATE (ESTER)
• METHYL 3B-HYDROXY-1alphaH,5alphaH-TROPANE-2beta-CARBOXYLATE BENZOATE (ESTER)
• 1-alpha-H,5-alpha-H-Tropane-2-beta-carboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate (ester) (8CI)
• 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, (1R,2R,3S,5S)- (9CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9329	93.29%
Caco-2	+	0.8795	87.95%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4796	47.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9260	92.60%
OATP1B3 inhibitior	+	0.9407	94.07%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	-	0.8304	83.04%
P-glycoprotein inhibitior	-	0.6269	62.69%
P-glycoprotein substrate	+	0.8809	88.09%
CYP3A4 substrate	+	0.6960	69.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3826	38.26%
CYP3A4 inhibition	-	0.9237	92.37%
CYP2C9 inhibition	-	0.9341	93.41%
CYP2C19 inhibition	-	0.9383	93.83%
CYP2D6 inhibition	-	0.5614	56.14%
CYP1A2 inhibition	-	0.8627	86.27%
CYP2C8 inhibition	-	0.8121	81.21%
CYP inhibitory promiscuity	-	0.9408	94.08%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6582	65.82%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.8227	82.27%
Skin corrosion	-	0.9533	95.33%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6986	69.86%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.8750	87.50%
skin sensitisation	-	0.9307	93.07%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7839	78.39%
Acute Oral Toxicity (c)	III	0.6875	68.75%
Estrogen receptor binding	-	0.6148	61.48%
Androgen receptor binding	-	0.8511	85.11%
Thyroid receptor binding	-	0.6822	68.22%
Glucocorticoid receptor binding	-	0.7607	76.07%
Aromatase binding	-	0.6159	61.59%
PPAR gamma	-	0.6710	67.10%
Honey bee toxicity	-	0.9251	92.51%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.8803	88.03%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL238	Q01959	Dopamine transporter	89.1 nM	IC50	via Super-PRED
CHEMBL240	Q12809	HERG	4.4 nM	IC50	via Super-PRED
CHEMBL222	P23975	Norepinephrine transporter	182 nM	Ki	via Super-PRED
CHEMBL228	P31645	Serotonin transporter	45 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.05%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.88%	90.17%
CHEMBL2581	P07339	Cathepsin D	94.24%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	92.71%	97.21%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	90.38%	94.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.37%	95.56%
CHEMBL2535	P11166	Glucose transporter	88.42%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.83%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	85.21%	91.19%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.60%	94.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.34%	99.23%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	84.29%	100.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	83.96%	97.53%
CHEMBL5028	O14672	ADAM10	82.78%	97.50%
CHEMBL4208	P20618	Proteasome component C5	82.54%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.85%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.80%	95.89%

Plants that contains it

• Erythroxylum coca
• Erythroxylum novogranatense

Cross-Links

• PubChem: 446220
• LOTUS: LTS0252766
• wikiData: Q41576