(1R,2R,6S)-19-(2-hydroxypentan-2-yl)-15-methoxy-3-methyl-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11,16-tetraen-11-ol

• ChemBase ID: 1292
• Molecular Formular: C25H33NO4
• Molecular Mass: 411.53382
• Monoisotopic Mass: 411.24095854
• SMILES: O1C2[C@]34[C@@]5([C@H](N(CC3)C)Cc3c4c1c(O)cc3)CC(C2(OC)C=C5)C(O)(CCC)C
• Canonical SMILES: CCCC(C1C[C@]23C=CC1(OC)C1[C@]43CCN([C@@H]2Cc2c4c(O1)c(O)cc2)C)(O)C
• InChI: InChI=1S/C25H33NO4/c1-5-8-22(2,28)17-14-23-9-10-25(17,29-4)21-24(23)11-12-26(3)18(23)13-15-6-7-16(27)20(30-21)19(15)24/h6-7,9-10,17-18,21,27-28H,5,8,11-14H2,1-4H3/t17?,18-,21?,22?,23-,24+,25?/m1/s1
• InChIKey: CAHCBJPUTCKATP-HBDRVVKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,6S)-19-(2-hydroxypentan-2-yl)-15-methoxy-3-methyl-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11,16-tetraen-11-ol
• IUPAC Traditional name: etorphine
• Brand Name: Immobilon
• Synonyms: Etorphine HCl; Etorphine Hydrochloride; M99; Etorphinum [INN-Latin]; DEA No. 9056; 7-alpha-Etorphine; 19-Propylorvinol; Etorphine

Database IDs

• CAS Number: 14521-96-1
• PubChem SID: 160964752; 46505591
• PubChem CID: 26721

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.213173
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.47010317
• LogD (pH = 7.4): 1.1065465
• Log P: 2.4724507
• Molar Refractivity: 116.5142 cm^3
• Polarizability: 45.393173 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.29
• LOG S: -3.56
• Solubility (Water): 1.12e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.79 [SANGSTER (1993)]

DETAILS

DrugBank - DB01497

• Drug Groups: illicit; experimental
• Description: A narcotic analgesic morphinan used as a sedative in veterinary practice. In Hong Kong, Etorphine is regulated under Schedule 1 of Hong Kong's Chapter 134 Dangerous Drugs Ordinance. It can only be used legally by health professionals and for university research purposes. The substance can be given by pharmacists under a prescription. In the US, Etorphine is listed as a Schedule I drug, although Etorphine hydrochloride is classified as Schedule II.
• Pharmacology: Etorphine is a synthetic cousin of morphine and 40,000 times more powerful. It can be produced from thebaine. It is most often used to immobilize elephants and other large mammals. Etorphine is only available legally for veterinary use and is strictly governed by law.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia