morphine (CHEBI:17303)

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CHEBI:17303 - morphine

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ChEBI Name	morphine

ChEBI ID	CHEBI:17303

Definition	A morphinane alkaloid that is a highly potent opiate analgesic psychoactive drug. Morphine acts directly on the central nervous system (CNS) to relieve pain but has a high potential for addiction, with tolerance and both physical and psychological dependence developing rapidly. Morphine is the most abundant opiate found in Papaver somniferum (the opium poppy).

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:44202, CHEBI:7001, CHEBI:14622, CHEBI:25419

Supplier Information	ChemicalBook:CB1384824, eMolecules:502037, ZINC000001600920

Download	Molfile XML SDF

more structures >>

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Wikipedia	License
β-Endorphin (beta-endorphin) is an endogenous opioid neuropeptide and peptide hormone that is produced in certain neurons within the central nervous system and peripheral nervous system. It is one of three endorphins that are produced in humans, the others being α-endorphin and γ-endorphin. There are multiple forms of β-endorphins with the full sequence of Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys-Asn-Ala-Ile-Ile-Lys-Asn-Ala-Tyr-Lys-Lys-Gly-Glu (31 amino acids) denoted as β-endorphin(1-31) and variants truncated to the first 26 and 27 amino acids as β-endorphin(1-26) and β-endorphin(1-27). However, β-endorphin(1-31) is the only form that possess a potent analgesic effect and it is the primary form located in the anterior pituitary gland, and regions such as the hypothalamus, midbrain, and amygdala. The first 16 amino acids are identical to α-endorphin. β-Endorphin is considered to be a part of the endogenous opioid and endorphin classes of neuropeptides; all of the established endogenous opioid peptides contain the same N-terminal amino acid sequence, Tyr-Gly-Gly-Phe, followed by either -Met or -Leu. Function of β-endorphin has been known to be associated with hunger, thrill, pain, maternal care, sexual behavior, and reward cognition. In the broadest sense, β-endorphin is primarily utilized in the body to reduce stress and maintain homeostasis. In behavioral research, studies have shown that β-endorphin is released via volume transmission into the ventricular system in response to a variety of stimuli, and novel stimuli in particular.
Read full article at Wikipedia

Formula

C17H19NO3

Net Charge

Average Mass

285.33770

Monoisotopic Mass

285.13649

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

SMILES

[H][C@]12C=C[C@H](O)[C@@H]3Oc4c(O)ccc5C[C@H]1N(C)CC[C@@]23c45

Metabolite of Species	Details
Papaver somniferum (NCBI:txid3469)	See: PubMed

Roles Classification
Chemical Role(s):	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects. Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	mu-opioid receptor agonist A compound that exhibits agonist activity at the mu-opioid receptor. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. opioid analgesic A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood. xenobiotic A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means. drug allergen Any drug which causes the onset of an allergic reaction. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

Application(s):	mu-opioid receptor agonist A compound that exhibits agonist activity at the mu-opioid receptor. vasodilator agent A drug used to cause dilation of the blood vessels. anaesthetic Substance which produces loss of feeling or sensation. opioid analgesic A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood. drug allergen Any drug which causes the onset of an allergic reaction. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	morphine (CHEBI:17303) has parent hydride morphinan (CHEBI:35649) morphine (CHEBI:17303) has role μ-opioid receptor agonist (CHEBI:55322) morphine (CHEBI:17303) has role anaesthetic (CHEBI:38867) morphine (CHEBI:17303) has role drug allergen (CHEBI:88188) morphine (CHEBI:17303) has role environmental contaminant (CHEBI:78298) morphine (CHEBI:17303) has role geroprotector (CHEBI:176497) morphine (CHEBI:17303) has role opioid analgesic (CHEBI:35482) morphine (CHEBI:17303) has role plant metabolite (CHEBI:76924) morphine (CHEBI:17303) has role vasodilator agent (CHEBI:35620) morphine (CHEBI:17303) has role xenobiotic (CHEBI:35703) morphine (CHEBI:17303) is a morphinane alkaloid (CHEBI:25418) morphine (CHEBI:17303) is a organic heteropentacyclic compound (CHEBI:38164) morphine (CHEBI:17303) is a tertiary amino compound (CHEBI:50996) morphine (CHEBI:17303) is conjugate base of morphine(1+) (CHEBI:58097)

Incoming	3-O-carboxymethylmorphine (CHEBI:233812) has functional parent morphine (CHEBI:17303) codeine (CHEBI:16714) has functional parent morphine (CHEBI:17303) codeinone (CHEBI:18399) has functional parent morphine (CHEBI:17303) heroin (CHEBI:27808) has functional parent morphine (CHEBI:17303) morphine-6-hemisuccinate (CHEBI:233811) has functional parent morphine (CHEBI:17303) morphinone (CHEBI:16315) has functional parent morphine (CHEBI:17303) myrophine (CHEBI:59860) has functional parent morphine (CHEBI:17303) morphine hydrochloride (CHEBI:55340) has part morphine (CHEBI:17303) morphine sulfate (CHEBI:7003) has part morphine (CHEBI:17303) morphine sulfate pentahydrate (CHEBI:50731) has part morphine (CHEBI:17303) morphine(1+) (CHEBI:58097) is conjugate acid of morphine (CHEBI:17303)

IUPAC Name

17-methyl-7,8-didehydro-4,5α-epoxymorphinan-3,6α-diol

Synonyms	Sources
(−)-morphine	ChemIDplus
(5α,6α)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol	ChEBI
(5α,6α)-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol	NIST Chemistry WebBook
(5R,6S,9R,13S,14R)-4,5-epoxy-N-methyl-7-morphinen-3,6-diol	ChemIDplus
(7R,7AS,12BS)-3-METHYL-2,3,4,4A,7,7A-HEXAHYDRO-1H-4,12-METHANO[1]BENZOFURO[3,2-E]ISOQUINOLINE-7,9-DIOL	PDBeChem
morfina	ChEBI
Morphia	ChemIDplus
Morphin	ChemIDplus
Morphine	KEGG COMPOUND
morphinum	ChemIDplus
morphium	ChemIDplus

Manual Xrefs	Databases
1845	DrugCentral
1Q0Y	PDB
2982	VSDB
C00001889	KNApSAcK
C01516	KEGG COMPOUND
D08233	KEGG DRUG
DB00295	DrugBank
MOI	PDBeChem
Morphine	Wikipedia
MORPHINE	MetaCyc
View more database links

Registry Numbers	Types	Sources
57-27-2	CAS Registry Number	ChemIDplus
57-27-2	CAS Registry Number	NIST Chemistry WebBook
93704	Reaxys Registry Number	Reaxys

Citations	Types	Sources
12593758	PubMed citation	Europe PMC
15019787	PubMed citation	Europe PMC
17171884	PubMed citation	Europe PMC
17667569	PubMed citation	Europe PMC
19371311	PubMed citation	Europe PMC
20071451	PubMed citation	Europe PMC
21061062	PubMed citation	Europe PMC
23292329	PubMed citation	Europe PMC
23325235	PubMed citation	Europe PMC
23555556	PubMed citation	Europe PMC
23927484	PubMed citation	Europe PMC
23988259	PubMed citation	Europe PMC
24096538	PubMed citation	Europe PMC
24306419	PubMed citation	Europe PMC
27735107	PubMed citation	Europe PMC
27815868	PubMed citation	Europe PMC
27866460	PubMed citation	Europe PMC
29368335	PubMed citation	Europe PMC
9231550	PubMed citation	Europe PMC

Last Modified

27 March 2025

General Comment
2014-10-29	Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag

CHEBI:17303 - morphine

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