(1S,5R,13R,14S,17R)-10-ethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18),15-tetraen-14-ol

• ChemBase ID: 1265
• Molecular Formular: C19H23NO3
• Molecular Mass: 313.39082
• Monoisotopic Mass: 313.1677936
• SMILES: O1[C@@H]2[C@]34[C@H]([C@H](N(CC3)C)Cc3c4c1c(OCC)cc3)C=C[C@@H]2O
• Canonical SMILES: CCOc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4C=C[C@@H]1O)C
• InChI: InChI=1S/C19H23NO3/c1-3-22-15-7-4-11-10-13-12-5-6-14(21)18-19(12,8-9-20(13)2)16(11)17(15)23-18/h4-7,12-14,18,21H,3,8-10H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1
• InChIKey: OGDVEMNWJVYAJL-LEPYJNQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S,17R)-10-ethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18),15-tetraen-14-ol; (1S,5R,13R,14S,17R)-10-ethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol
• IUPAC Traditional name: ethylmorphine
• Synonyms: Morphine 3-ethyl ether; Ethylmorphine; Codethyline; Dionine; Ethyl morphine; Ethylmorphine

Database IDs

• CAS Number: 76-58-4
• EC Number: 200-970-7
• MDL Number: MFCD00083327
• PubChem SID: 160964725; 46505092; 24894676
• PubChem CID: 5359271
• ATC CODE: R05DA01
• Chemspider ID: 4514250
• DrugBank ID: DB01466
• Unique Ingredient Identifier: RWO67D87EU
• Wikipedia Title: Ethylmorphine

CALCULATED PROPERTIES

JChem

• LogD (pH = 5.5): -1.5852752
• LogD (pH = 7.4): -0.08994477
• Log P: 1.6997592
• Molar Refractivity: 89.3533 cm^3
• Polarizability: 34.45052 Å^3
• Polar Surface Area: 41.93 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 13.78274
• H Acceptors: 4
• H Donor: 1

ALOGPS 2.1

• Log P: 1.72
• LOG S: -2.57
• Solubility (Water): 8.35e-01 g/l

PROPERTIES

Physical Property

• Solubility: 2.61 mg/mL at 20 oC [SEIDELL,A (1941)]

Safety Information

• RTECS: QD0850000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Pharmacology Properties

• Legal Status: Schedule II (Single-Entity), Schedule III (In Combination Products)

DETAILS

DrugBank - DB01466

• Drug Groups: illicit; experimental
• Description: A narcotic analgesic and antitussive. It is metabolized in the liver by ethylmorphine-N-demethylase and used as an indicator of liver function. It is not marketed in the US but is approved for use in various countries around the world. In the US it is a schedule II drug (single-entity) and schedule III drug (in combination products).
• Indication: Ethylmorphine is an analgesic used for pain relief.
• Pharmacology: Ethylmorphine is metabolized by the enzyme cytochrome P450 2D6 to morphine. Morphine is a narcotic pain management agent indicated for the relief of pain in patients who require opioid analgesics for more than a few days. Morphine interacts predominantly with the opioid mu-receptor. These mu-binding sites are discretely distributed in the human brain, with high densities in the posterior amygdala, hypothalamus, thalamus, nucleus caudatus, putamen, and certain cortical areas. They are also found on the terminal axons of primary afferents within laminae I and II (substantia gelatinosa) of the spinal cord and in the spinal nucleus of the trigeminal nerve. In clinical settings, morphine exerts its principal pharmacological effect on the central nervous system and gastrointestinal tract. Its primary actions of therapeutic value are analgesia and sedation. Morphine appears to increase the patient's tolerance for pain and to decrease discomfort, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Opioids also produce respiratory depression by direct action on brain stem respiratory centers.
• Affected Organisms: Humans and other mammals
• Biotransformation: After ingestion, ethylmorphine is converted to morphine in the human liver by the CYP450-isozyme CYP2D6, similarly to codeine.
• References: Aasmundstad TA, Xu BQ, Johansson I, Ripel A, Bjorneboe A, Christophersen AS, Bodd E, Morland J: Biotransformation and pharmacokinetics of ethylmorphine after a single oral dose. Br J Clin Pharmacol. 1995 Jun;39(6):611-20. [Pubmed] ; Xu BQ, Aasmundstad TA, Lillekjendlie B, Bjorneboe A, Christophersen AS, Morland J: Effects of ethanol on ethylmorphine metabolism in isolated rat hepatocytes: characterization by means of a multicompartmental model. Pharmacol Toxicol. 1997 Apr;80(4):171-81. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - E8512

Biochem/physiol Actions
Narcotic analgesic; antitussive

REFERENCES

• Aasmundstad TA, Xu BQ, Johansson I, Ripel A, Bjorneboe A, Christophersen AS, Bodd E, Morland J: Biotransformation and pharmacokinetics of ethylmorphine after a single oral dose. Br J Clin Pharmacol. 1995 Jun;39(6):611-20. Pubmed
• Xu BQ, Aasmundstad TA, Lillekjendlie B, Bjorneboe A, Christophersen AS, Morland J: Effects of ethanol on ethylmorphine metabolism in isolated rat hepatocytes: characterization by means of a multicompartmental model. Pharmacol Toxicol. 1997 Apr;80(4):171-81. Pubmed