Morphine hydrochlorideProduct ingredient for Morphine

Name
Morphine hydrochloride
Drug Entry
Morphine

Morphine is the main alkaloid of opium and it was first obtained from the poppy seeds in 1805.1 It is the most potent analgesic for chronic pain but its use is limited due to the induction of tolerance, severe withdrawal symptoms and high risk of relapse and abuse.2 In its pure form, morphine is ten times more potent than opium and due to this property, it was used extensively in the US Civil War which derived in approximately 400,000 addicted soldiers. After this event, around the second half of the nineteenth-century, the science made several efforts to find a less addictive alternative which brought the synthesis of heroin. However, morphine is still the precursor to other opioids such as codeine, fentanyl, methadone, hydrocodone, hydromorphone, meperidine, and oxycodone.11 Morphine's first official product was developed by West-Ward Pharmaceuticals Int. and FDA approved in 1984.10

Accession Number
DBSALT001753
Structure
Thumb
Synonyms
Morphine HCl
UNII
J28GE0ROVX
CAS Number
52-26-6
Weight
Average: 321.8
Monoisotopic: 321.1131712
Chemical Formula
C17H20ClNO3
InChI Key
XCKKIKBIPZJUET-VYKNHSEDSA-N
InChI
InChI=1S/C17H19NO3.ClH/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;1H/t10-,11+,13-,16-,17-;/m0./s1
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 hydrochloride
SMILES
Cl.CN1CC[C@]23[C@H]4OC5=C(O)C=CC(C[C@@H]1[C@@H]2C=C[C@@H]4O)=C35
External Links
ChemSpider
4576542
ChEBI
55340
ChEMBL
CHEMBL556578
Wikipedia
Morphine
Predicted Properties
PropertyValueSource
Water Solubility10.2 mg/mLALOGPS
logP0.99ALOGPS
logP0.9ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)10.26ChemAxon
pKa (Strongest Basic)9.12ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.93 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity80.12 m3·mol-1ChemAxon
Polarizability30 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon