Oramorph

Morphine

Clinical data
Pronunciation	/ˈmɔːrfiːn/
Trade names	MScontin, Oramorph, Sevredol, and others
AHFS/Drugs.com	Monograph
Pregnancy category	AU: C US: C (Risk not ruled out)
Dependence liability	Physical: High Psychological: Moderate
Addiction liability	High
Routes of administration	Inhalation (smoking), insufflation (snorting), by mouth (PO), rectal, subcutaneous (SC), intramuscular (IM), intravenous (IV), epidural, and intrathecal (IT)
Drug class	opiate
ATC code	N02AA01 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage III (Special prescription form required) NZ: Class B UK: Class A US: Schedule II UN: Narcotic Schedules I and III
Pharmacokinetic data
Bioavailability	20% to 40% (by mouth), 36% to 71% (rectally), 100% (IV/IM)
Protein binding	30% to 40%
Metabolism	Hepatic 90%
Onset of action	5 min (IV), 15 min (IM), 20 min (PO)
Biological half-life	2 h to 3 h
Duration of action	3 h to 7 h
Excretion	Renal 90%, biliary 10%
Identifiers
IUPAC name (4R,4aR,7S,7aR,12bS)-3-Methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
CAS Number	57-27-2 Y 64-31-3 (neutral sulfate), 52-26-6 (hydrochloride)
PubChem CID	5288826
IUPHAR/BPS	1627
DrugBank	DB00295 Y
ChemSpider	4450907 Y
UNII	76I7G6D29C
KEGG	D08233 Y
ChEBI	CHEBI:17303 Y
ChEMBL	CHEMBL70 Y
ECHA InfoCard	100.000.291
Chemical and physical data
Formula	C17H19NO3
Molar mass	285.34 g/mol
3D model (JSmol)	Interactive image
Solubility in water	HCl & sulf.: 60 mg/mL (20 °C)
SMILES CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5
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 Y Key:BQJCRHHNABKAKU-KBQPJGBKSA-N Y

Morphine is a pain medication of the opiate type which is found naturally in a number of plants and animals. It acts directly on the central nervous system (CNS) to decrease the feeling of pain. It can be taken for both acute pain and chronic pain. Morphine is frequently used for pain from myocardial infarction and during labour. It can be given by mouth, by injection into a muscle, by injecting under the skin, intravenously, into the space around the spinal cord, or rectally. Maximum effect is around 20 minutes when given intravenously and 60 min when given by mouth, while duration of effect is between 3 h and 7 h. Long-acting formulations also exist.

Potentially serious side effects include a decreased respiratory effort and low blood pressure. Morphine has a high potential for addiction and abuse. If the dose is reduced after long-term use, withdrawal may occur. Common side effects include drowsiness, vomiting, and constipation. Caution is advised when used during pregnancy or breast feeding, as morphine will affect the baby.

Morphine was first isolated between 1803 and 1805 by Friedrich Sertürner. This is generally believed to be the first isolation of an active ingredient from a plant.Merck began marketing it commercially in 1827. Morphine was more widely used after the invention of the hypodermic syringe in 1853–1855. Sertürner originally named the substance morphium after the Greek god of dreams, Morpheus, as it has a tendency to cause sleep.