(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraene-10,14-diol

• ChemBase ID: 180
• Molecular Formular: C17H19NO3
• Molecular Mass: 285.33766
• Monoisotopic Mass: 285.13649347
• SMILES: O1[C@@H]2[C@]34[C@H]([C@H](N(CC3)C)Cc3c4c1c(O)cc3)C=C[C@@H]2O
• Canonical SMILES: O[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1O
• InChI: InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1
• InChIKey: BQJCRHHNABKAKU-KBQPJGBKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraene-10,14-diol; (1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraene-10,14-diol
• IUPAC Traditional name: morphine; morph
• Brand Name: M-Eslon; M.O.S; MS/L; MS/S; MSIR; Meconium; Morfina; Morphia; Morphine Extra-Forte; Morphine Forte; Morphine H.P; Morphinism; Morphitec; Morphium; Moscontin; Ms Contin; Nepenthe; OMS Concentrate; Oramorph SR; Ospalivina; RMS Uniserts; Rescudose; Roxanol; Roxanol 100; Roxanol UD; Statex; Statex Drops; l-Morphine; Apokyn; Astramorph PF; Avinza; Depodur; Dulcontin; Duramorph PF; Duromorph; Epimorph; Kadian; Mscontin, Oramorph
• Synonyms: Morphine solution; (-)-Heroin hydrochloride; (-)-Morphine; D-(-)-Morphine; Diacetylmorphine hydrochloride; Diamorphine hydrochloride; Heroin hydrochloride; Heroine hydrochloride; Morphine Sulfate; Morphinum; O,O'-Diacetylmorphine hydrochloride; Morphin; Morphina; morphine; Morphine; 吗啡 溶液

Database IDs

• CAS Number: 57-27-2
• EC Number: 200-659-6
• MDL Number: MFCD00153032
• PubChem SID: 160963643; 46505161
• PubChem CID: 5288826
• CHEBI ID: 17303
• ATC CODE: N02AA01
• CHEMBL: 70
• Chemspider ID: 4450907
• DrugBank ID: DB00295
• IUPHAR ligand ID: 1627
• KEGG ID: D08233
• Unique Ingredient Identifier: 76I7G6D29C
• Wikipedia Title: Morphine

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.2556095
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.0906866
• LogD (pH = 7.4): -0.60061675
• Log P: 0.8952108
• Molar Refractivity: 80.1224 cm^3
• Polarizability: 30.698988 Å^3
• Polar Surface Area: 52.93 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.99
• LOG S: -1.45
• Solubility (Water): 1.02e+01 g/l

PROPERTIES

Physical Property

• Solubility: 149 mg/L (60 mg/mL for sulfate salt); HCl & sulf.: 60 mg/mL (20°C)
• Flash Point: 11 °C; 51.8 °F
• Hydrophobicity(logP): 0.8

Safety Information

• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1230
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301-H311-H331-H370
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1230 3/PG 2
• Drug Control: kontrollierte Droge in Deutschlandregulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Pharmacology Properties

• Admin Routes: Inhalation (smoking), insufflation (snorting), oral, rectal, subcutaneous (S.C), intramuscular (I.M), intravenous (I.V), and intrathecal (I.T)
• Bioavailability: 20-40% (oral), 36-71% (rectally), 100% (IV/IM)
• Dependency Liability: High
• Excretion: Renal 90%, biliary 10%
• Half Life: 2–3 h
• Metabolism: Hepatic 90%
• Protein Bound: 30–40%
• Legal Status: S8 (Australia); Schedule I (Canada); Schedule II (US)
• Pregnancy Category: C (Australia); C (US)

Product Information

• Concentration: 1 mg/mL in methanol
• Grade: drug standard
• Empirical Formula (Hill Notation): C17H19NO3

DETAILS

DrugBank - DB00295

• Drug Groups: approved; investigational
• Description: The principal alkaloid in opium and the prototype opiate analgesic and narcotic. Morphine has widespread effects in the central nervous system and on smooth muscle. [PubChem]
• Indication: For the relief and treatment of severe pain.
• Pharmacology: 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.
• Toxicity: LD₅₀ = 461 mg/kg (rat, oral), 600 mg/kg (mouse, oral). Human lethal dose by ingestion is 120-250 mg of morphine sulfate. Symptoms of overdose include cold, clammy skin, flaccid muscles, fluid in the lungs, lowered blood pressure, "pinpoint" or dilated pupils, sleepiness leading to stupor and coma, slowed breathing, and slow pulse rate.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic (90%), converted to dihydromorphinone and normorphine. Also converted to morphine-3-glucuronide (M3G) and morphine-6-glucuronide. Virtually all morphine is converted to glucuronide metabolites; only a small fraction (less than 5%) of absorbed morphine is demethylated.
• Absorption: Bioavailability is approximately 30%.
• Half Life: 2-4 hours
• Protein Binding: 30-40%
• Elimination: A small amount of glucuronide conjugates are excreted in bile, with minor enterohepatic recycling. Seven to 10% of administered morphine sulfate is excreted in the feces.
• Distribution: * 1 to 6 L/kg
• Clearance: * 20 – 30 mL/min/kg [Adult]; * 1852 +/- 116 mL/min [Chinese]; * 1495 +/- 80 mL/min [Caucasian]
• References: Kilpatrick GJ, Smith TW: Morphine-6-glucuronide: actions and mechanisms. Med Res Rev. 2005 Sep;25(5):521-44. [Pubmed] ; Loguinov AV, Anderson LM, Crosby GJ, Yukhananov RY: Gene expression following acute morphine administration. Physiol Genomics. 2001 Aug 28;6(3):169-81. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - 610062

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 610062.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• Kilpatrick GJ, Smith TW: Morphine-6-glucuronide: actions and mechanisms. Med Res Rev. 2005 Sep;25(5):521-44. Pubmed
• Loguinov AV, Anderson LM, Crosby GJ, Yukhananov RY: Gene expression following acute morphine administration. Physiol Genomics. 2001 Aug 28;6(3):169-81. Pubmed