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57-27-2 molecular structure
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(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 and InChIs

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

Cite this record

CBID:180 http://www.chembase.cn/molecule-180.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraene-10,14-diol
IUPAC Traditional name
morph
morphine
Brand Name
Apokyn
Astramorph PF
Avinza
Depodur
Dulcontin
Duramorph PF
Duromorph
Epimorph
Kadian
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
Mscontin, Oramorph
Synonyms
(-)-Heroin hydrochloride
(-)-Morphine
D-(-)-Morphine
Diacetylmorphine hydrochloride
Diamorphine hydrochloride
Heroin hydrochloride
Heroine hydrochloride
Morphine Sulfate
Morphinum
O,O'-Diacetylmorphine hydrochloride
Morphin
Morphina
morphine
Morphine solution
Morphine
吗啡 溶液
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
610062 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.2556095  H Acceptors
H Donor LogD (pH = 5.5) -2.0906866 
LogD (pH = 7.4) -0.60061675  Log P 0.8952108 
Molar Refractivity 80.1224 cm3 Polarizability 30.698988 Å3
Polar Surface Area 52.93 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.99  LOG S -1.45 
Solubility (Water) 1.02e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
149 mg/L (60 mg/mL for sulfate salt) expand Show data source
HCl & sulf.: 60 mg/mL (20°C) expand Show data source
Flash Point
11 °C expand Show data source
51.8 °F expand Show data source
Hydrophobicity(logP)
0.8 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Toxic Toxic (T) expand Show data source
UN Number
1230 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
1 expand Show data source
Hazard Class
3 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
11-23/24/25-39/23/24/25 expand Show data source
Safety Statements
7-16-36/37-45 expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H225-H301-H311-H331-H370 expand Show data source
GHS Precautionary statements
P210-P260-P280-P301 + P310-P311 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 1230 3/PG 2 expand Show data source
Drug Control
kontrollierte Droge in Deutschlandregulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Storage Temperature
-20°C expand Show data source
Admin Routes
Inhalation (smoking), insufflation (snorting), oral, rectal, subcutaneous (S.C), intramuscular (I.M), intravenous (I.V), and intrathecal (I.T) expand Show data source
Bioavailability
20-40% (oral), 36-71% (rectally), 100% (IV/IM) expand Show data source
Dependency Liability
High expand Show data source
Excretion
Renal 90%, biliary 10% expand Show data source
Half Life
2–3 h expand Show data source
Metabolism
Hepatic 90% expand Show data source
Protein Bound
30–40% expand Show data source
Legal Status
S8 (Australia) expand Show data source
Schedule I (Canada) expand Show data source
Schedule II (US) expand Show data source
Pregnancy Category
C (Australia) expand Show data source
C (US) expand Show data source
Concentration
1 mg/mL in methanol expand Show data source
Grade
drug standard expand Show data source
Empirical Formula (Hill Notation)
C17H19NO3 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich DrugBank DrugBank
Sigma Aldrich - 610062 external link
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.
DrugBank - DB00295 external link
Item Information
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

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

PATENTS

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