DIAMORPHINE

First marketed in 1827

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H23NO5
Molecular Weight	369.411
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CC[C@]23[C@H]4OC5=C(OC(C)=O)C=CC(C[C@@H]1[C@@H]2C=C[C@@H]4OC(C)=O)=C35

InChI

InChIKey=GVGLGOZIDCSQPN-PVHGPHFFSA-N

InChI=1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H23NO5
Molecular Weight	369.411
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018565s022lbl_Duramorph.pdf | https://www.ncbi.nlm.nih.gov/pubmed/16530171

Morphine is one of the most important and widely used opioid for the treatment of chronic and acute pain: the very wide interindividual variability in the patients’ response to the drug may have genetic derivations. Sulphate salt of morphine sold under the many brand names, one of them, DURAMORPH, which is indicated for the management of pain severe enough to require use of an opioid analgesic by intravenous administration, and for which alternative treatments are not expected to be adequate. In addition for the epidural or intrathecal management of pain without attendant loss of motor, sensory, or sympathetic function. Morphine is a full opioid agonist and is relatively selective for the mu-opioid receptor, although it can bind to other opioid receptors at higher doses. The principal therapeutic action of morphine is analgesia. Like all full opioid agonists, there is no ceiling effect for analgesia with morphine. The precise mechanism of the analgesic action is unknown. However, specific CNS opioid receptors for endogenous compounds with opioid-like activity have been identified throughout the brain and spinal cord and are thought to play a role in the analgesic effects of this drug. Morphine has a high potential for addiction and abuse. Common side effects include drowsiness, vomiting, and constipation. Caution is advised when used during pregnancy or breast-feeding, as morphine will affect the baby.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 231 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16580639	Agonist 2752
Kappa-type opioid receptor 61 Target ID: P41145 Gene ID: 4986.0 Gene Symbol: OPRK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16530171	Agonist 2752
Delta-type opioid receptor 46 Target ID: P41143 Gene ID: 4985.0 Gene Symbol: OPRD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10670411	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain severe 27 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018565s022lbl_Duramorph.pdf	Palliative		Approved 8583	DURAMORPH PF Approved Use DURAMORPH is indicated for: the management of pain severe enough to require use of an opioid analgesic by intravenous administration, and for which alternative treatments are not expected to be adequate.For the epidural or intrathecal management of pain without attendant loss of motor, sensory, or sympathetic function. Launch Date 1984

C_max

Value	Dose	Co-administered	Analyte	Population
63 nM EXPERIMENT https://link.springer.com/article/10.2165/00003088-199324040-00007	2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered:		MORPHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
165 nM × h EXPERIMENT https://link.springer.com/article/10.2165/00003088-199324040-00007	2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered:		MORPHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
15.1 h EXPERIMENT https://link.springer.com/article/10.2165/00003088-199324040-00007	2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered:		MORPHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
65% EXPERIMENT https://link.springer.com/article/10.2165/00003088-199324040-00007	2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered:		MORPHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2720580/	healthy, adult Health Status: healthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/2720580/	Sources: https://pubmed.ncbi.nlm.nih.gov/2720580/
180 mg 1 times / day steady, oral Dose: 180 mg, 1 times / day Route: oral Route: steady Dose: 180 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28530786/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/28530786/	Sources: https://pubmed.ncbi.nlm.nih.gov/28530786/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741	CYP1A2 1197 CYP2C19 1119 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2E1 729 UGT2B7 456 UGT1A1 479 UGT1A3 470 UGT1A6 343 UGT1A8 323 UGT1A9 423 UGT1A10 331 OCT1 393 P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Metabolite
P-gp 1932	inhibitor 4027 Sources: https://pubs.asahq.org/anesthesiology/article/96/4/913/39246/Interaction-of-Morphine-Fentanyl-Sufentanil Page: -	no
P-gp 1932	inhibitor 4027 Sources: https://pubs.asahq.org/anesthesiology/article/96/4/913/39246/Interaction-of-Morphine-Fentanyl-Sufentanil Page: -	no	morphine-3-glucuronide 27
P-gp 1932	inhibitor 4027 Sources: https://pubs.asahq.org/anesthesiology/article/96/4/913/39246/Interaction-of-Morphine-Fentanyl-Sufentanil Page: -	no	morphine-6-glucuronide 27

Drug as victim

Target	Modality	Activity	Metabolite
CYP1A2 1197	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1080/0049825031000121608 Page: -	no
CYP2A6 626	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1080/0049825031000121608 Page: -	no
CYP2B6 776	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1080/0049825031000121608 Page: -	no
CYP2E1 729	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1080/0049825031000121608 Page: -	no
CYP2D6 1388	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1080/0049825031000121608 Page: -	yes [Km 10100 uM]
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: -	yes [Km 12600 uM]
CYP3A4 1946	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1080/0049825031000121608 Page: -	yes [Km 14150 uM]
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: -	yes [Km 18000 uM]
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: -	yes [Km 18700 uM]
CYP2C9 1193	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1080/0049825031000121608 Page: -	yes [Km 25400 uM]
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: -	yes [Km 2600 uM]
OCT1 393	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0006295213003900 Page: -	yes [Km 3.4 uM]
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: -	yes [Km 3200 uM]
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: -	yes [Km 37400 uM]
UGT2B7 456	substrate 4014 Sources: https://molpharm.aspetjournals.org/content/67/3/665.short Page: -	yes [Km 380 uM]
CYP2C8 810	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1080/0049825031000121608 Page: -	yes [Km 4800 uM]
CYP2C19 1119	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1080/0049825031000121608 Page: -	yes [Km 6400 uM]
P-gp 2052	substrate 4014 Sources: https://pubs.asahq.org/anesthesiology/article/96/4/913/39246/Interaction-of-Morphine-Fentanyl-Sufentanil Page: -	yes
P-gp 2052	substrate 4014 Sources: https://pubs.asahq.org/anesthesiology/article/96/4/913/39246/Interaction-of-Morphine-Fentanyl-Sufentanil Page: -	yes	morphine-3-glucuronide 27
P-gp 2052	substrate 4014 Sources: https://pubs.asahq.org/anesthesiology/article/96/4/913/39246/Interaction-of-Morphine-Fentanyl-Sufentanil Page: -	yes	morphine-6-glucuronide 27

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:17303	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17303
eMolecules	6843460	https://www.emolecules.com/cgi-bin/more?vid=6843460
ZINC	ZINC000003812983	http://zinc15.docking.org/substances/ZINC000003812983

PubMed

Title	Date	PubMed
Catalepsy induced by morphine or haloperidol: effects of apomorphine and anticholinergic drugs.	1976 Aug	10058
Psychopharmacological studies on (--)-nuciferine and its Hofmann degradation product atherosperminine.	1978 Sep 15	100809
Side-effects of epidural infusions of opioid bupivacaine mixtures.	1998 Dec	10193215
Butorphanol agonist effects and acute physical dependence in opioid abusers: comparison with morphine.	1998 Dec 1	10933337
Reduction of dyskinesia and induction of akinesia induced by morphine in two parkinsonian patients with severe sciatica.	1999	10907730
Extrapyramidal side-effects from droperidol mixed with morphine for patient-controlled analgesia in two children.	1999	10411778
Efficacy and complications of morphine infusions in postoperative paediatric patients.	1999	10411768
The involvement of noradrenergic transmission in the morphine-induced locomotor hyperactivity in mice withdrawn from repeated morphine treatment.	1999 Apr	10323593
[Opioid receptor knockout mice].	1999 Dec	10803207
Preliminary UK experience of dexmedetomidine, a novel agent for postoperative sedation in the intensive care unit.	1999 Dec	10594409
[The discriminative stimulus properties of naloxone during dissociative learning in a Y maze in morphine-dependent rats].	1999 Jan-Feb	10330710
The effects of dopamine D2 and D3 antagonists on spontaneous motor activity and morphine-induced hyperactivity in male mice.	1999 Mar	10227083
The effects of quinine and 4-aminopyridine on conditioned place preference and changes in motor activity induced by morphine in rats.	1999 May	10390729
Controlling myoclonus after high-dosage morphine infusions.	1999 May 15	10365727
Patient-controlled analgesia with morphine plus lysine acetyl salicylate.	1999 Oct	10512278
Effects of SCH 23390, raclopride, and haloperidol on morphine withdrawal-induced aggression in male mice.	1999 Sep	10495006
Peroperative titration of morphine improves immediate postoperative analgesia after total hip arthroplasty.	2000 Apr	10764173
Orphanin FQ/nociceptin inhibits morphine withdrawal.	2000 Jan 14	10680585
Morphine-induced macrophage apoptosis: the role of transforming growth factor-beta.	2000 May	10809959
Insidious intoxication after morphine treatment in renal failure: delayed onset of morphine-6-glucuronide action.	2000 May	10781294
Systemic naloxone enhances cerebral blood flow in anesthetized morphine-dependent rats.	2000 Nov 24	11090647
Enhanced spinal nociceptin receptor expression develops morphine tolerance and dependence.	2000 Oct 15	11027224
Inhaled morphine to relieve dyspnea in advanced cystic fibrosis lung disease.	2000 Sep	10973044
Effect of dexmedetomidine on the release of [3H]-noradrenaline from rat kidney cortex slices: characterization of alpha2-adrenoceptor.	2001 Apr	11137626
Large-dose oral dextromethorphan as an adjunct to patient-controlled analgesia with morphine after knee surgery.	2001 Feb	11159249
A single nucleotide polymorphic mutation in the human mu-opioid receptor severely impairs receptor signaling.	2001 Feb 2	11067846
Multicentre randomised controlled trial of nasal diamorphine for analgesia in children and teenagers with clinical fractures.	2001 Feb 3	11157525
Comparison of three methods to find the vapor activity of a hydration step.	2001 Jan	11154907
Cellular and synaptic adaptations mediating opioid dependence.	2001 Jan	11152760
Randomized clinical trial of diathermy versus scalpel incision in elective midline laparotomy.	2001 Jan	11136307
Demographic and therapeutic determinants of pain reactivity in very low birth weight neonates at 32 Weeks' postconceptional Age.	2001 Jan	11134442
Clonidine combined with a long acting local anesthetic does not prolong postoperative analgesia after brachial plexus block but does induce hemodynamic changes.	2001 Jan	11133627
Bupivacaine wound instillation via an electronic patient-controlled analgesia device and a double-catheter system does not decrease postoperative pain or opioid requirements after major abdominal surgery.	2001 Jan	11133625
A randomized, double-blinded comparison of intrathecal morphine, sufentanil and their combination versus IV morphine patient-controlled analgesia for postthoracotomy pain.	2001 Jan	11133596
Occurrence of morphine tolerance and dependence in the nucleus paragigantocellularis neurons.	2001 Jan 5	11137862
Morphine induces short-lived changes in G-protein gene expression in rat prefrontal cortex.	2001 Jan 5	11137853

Patents

Sample Use Guides

In Vivo Use Guide

Dosage for Intravenous Administration: Adult Dosage: The initial dose of morphine should be 2 mg to 10 mg/70 kg of body weight. Dosage for Epidural Administration: Adult Dosage: Initial injection of 5 mg in the lumbar region may provide satisfactory pain relief for up to 24 hours. If adequate pain relief is not achieved within one hour, careful administration of incremental doses of 1 to 2 mg at intervals sufficient to assess effectiveness may be given. Do not administer more than 10 mg per 24 hours. Dosage for Intrathecal Administration: Adult Dosage: Intrathecal dosage is usually 1/10 that of epidural dosage. A single injection of 0.2 to 1 mg may provide satisfactory pain relief for up to 24 hours. (Caution: this is only 0.4 to 2 mL of the 5 mg/10 mL ampul or 0.2 to 1 mL of the 10 mg/10 mL ampul of DURAMORPH). Do not inject intrathecally more than 2 mL of the 5 mg/10 mL ampul or 1 mL of the 10 mg/10 mLampul. Repeated intrathecal injections of DURAMORPH are not recommended. If pain recurs, consider consider alternative routes of administration.

Route of Administration: Other

In Vitro Use Guide

It was evaluated the effect of morphine on the proangiogenic interaction taking place between macrophages and breast cancer cells in vitro. It was shown, that morphine prevents, in part via modulating VEGF-A expression, the pro-angiogenic interaction between macrophages and breast cancer cells. The conditioned medium (CM) from breast cancer cells co-cultured with macrophages elicited endothelial cell proliferation and tube formation. This effect was inhibited if the co-culture occurred in the presence of morphine (20 uM). Using a mouse antibody array, it was identified several angiogenesis-regulating factors differentially expressed in the CM of co-cultured cells prepared in the presence or absence of morphine (o, 10, 20 uM), amongst which interleukin (IL)-6, tumour necrosis factor (TNF)-α and vascular endothelial growth factor (VEGF)-A. VEGF was induced in both cell types by the co-culture and this was prevented by morphine in a non-naloxone reversible fashion. The effect of CM from co-cultured cells on endothelial tube formation, but not proliferation, was prevented by anti-VEGF neutralizing antibody

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:34:37 GMT 2025` Edited by `admin` on `Mon Mar 31 17:34:37 GMT 2025`
Record UNII	70D95007SX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIACETYLMORPHINE

Preferred Name

English

DIAMORPHINE

Common Name

English

DIAPHORM

Common Name

English

DIAMORPHINE-

Common Name

English

DIACETYLMORPHINE [MI]

Common Name

English

IDS-NH-001(SECT.3)

Code

English

ECLORION

Common Name

English

HEROIN [HSDB]

Common Name

English

Diamorphine [WHO-DD]

Common Name

English

(5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-17-METHYLMORPHINAN-3,6-DIOL DIACETATE (ESTER)

Common Name

English

CHINA WHITE

Common Name

English

HEROIN

Common Name

English

IDS-NH-001

Code

English

J6.494G

Code

English

ACETOMORPHINE

Common Name

English

MORPHACETIN

Common Name

English

Classification Tree Code System Code

WHO-ATC

N07BC06