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Identification
Name Heroin
Accession Number DB01452
Type small molecule
Groups illicit, approved
Description

A narcotic analgesic that may be habit-forming. It is a controlled substance (opium derivative) listed in the U.S. Code of Federal Regulations, Title 21 Parts 329.1, 1308.11 (1987). Sale is forbidden in the United States by Federal statute. (Merck Index, 11th ed) Internationally, heroin is controlled under Schedules I and IV of the Single Convention on Narcotic Drugs. It is illegal to manufacture, possess, or sell heroin in the United States and the UK. However, under the name diamorphine, heroin is a legal prescription drug in the United Kingdom.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
diacetylmorphine
diamorphine
morphine diacetate
Salts
  • Heroin hydrochloride
Brand names Not Available
Brand mixtures Not Available
Categories
  • Narcotics
  • Analgesics
  • Analgesics, Opioid
CAS number 561-27-3
Weight Average: 369.411
Monoisotopic: 369.157622851
Chemical Formula C21H23NO5
InChI Key InChIKey=GVGLGOZIDCSQPN-PVHGPHFFSA-N
InChI
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
Plain Text
IUPAC Name
(1S,5R,13R,14S,17R)-10-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-yl acetate
SMILES
[H][C@@]12OC3=C(OC(C)=O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2OC(C)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Used in the treatment of acute pain, myocardial infarction, acute pulmonary oedema, and chronic pain.
Pharmacodynamics The onset of heroin's effects is dependent on the method of administration. Taken orally, heroin is totally metabolized in vivo into morphine before crossing the blood-brain barrier; so the effects are the same as oral morphine. Take by injection, heroin crosses into the brain. Once in the brain, heroin is rapidly metabolized into morphine by removal of the acetyl groups, therefore, it is known as a prodrug. It is the morphine molecule that then binds with opioid receptors and produces the subjective effects of the heroin high.
Mechanism of action Heroin is a mu-opioid agonist. It acts on endogenous mu-opioid receptors that are spread in discrete packets throughout the brain, spinal cord and gut in almost all mammals. Heroin, along with other opioids, are agonists to four endogenous neurotransmitters. They are beta-endorphin, dynorphin, leu-enkephalin, and met-enkephalin. The body responds to heroin in the brain by reducing (and sometimes stopping) production of the endogenous opioids when heroin is present. Endorphins are regularly released in the brain and nerves, attenuating pain. Their other functions are still obscure, but are probably related to the effects produced by heroin besides analgesia (antitussin, anti-diarrheal).
Absorption Bioavailability is less than 35%.
Volume of distribution Not Available
Protein binding 0% (morphine metabolite 35%)
Metabolism Hepatic.
Route of elimination 90% renal as glucuronides, rest biliary
Half life <10 minutes
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00407 Heroin Pathway SMP00407
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms
Form Route Strength
Powder, for solution Intravenous
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 173 °C PhysProp
boiling point 272-274 °C at 1.20E+01 mm Hg PhysProp
water solubility 600 mg/L (at 25 °C) SEIDELL,A (1941)
logP 1.58 AVDEEF,A ET AL. (1996)
pKa 7.95 (at 25 °C) AVDEEF,A ET AL. (1996)
Predicted Properties
Property Value Source
water solubility 2.66e-01 g/l ALOGPS
logP 2.3 ALOGPS
logP 1.55 ChemAxon
logS -3.1 ALOGPS
pKa (strongest basic) 9.1 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 65.07 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 98.43 ChemAxon
polarizability 37.9 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Tschacher W, Haemmig R, Jacobshagen N: Time series modeling of heroin and morphine drug action. Psychopharmacology (Berl). 2003 Jan;165(2):188-93. Epub 2002 Oct 29. Pubmed
External Links
Resource Link
KEGG Compound C06534 Link_out
PubChem Compound 5462328 Link_out
PubChem Substance 46506839 Link_out
ChemSpider 4575379 Link_out
ChEBI 27808 Link_out
ChEMBL 27808 Link_out
PharmGKB PA452619 Link_out
Drugs.com http://www.drugs.com/heroin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Heroin Link_out
ATC Codes
  • N02AA09
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (18.8 KB)
Interactions
Drug Interactions
Drug Interaction
Alvimopan Increases levels by receptor binding competition. Discontinue opioid administration at least 7 days prior to administrating Alvimopan.
Cimetidine Cimetidine increases the effect of the narcotic
Food Interactions
  • Avoid alcohol
  • To avoid constipation: increase your daily intake of fiber (beans, whole grains, vegetables).
Targets

1. Mu-type opioid receptor

Pharmacological action: yes
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin

Organism class: human
UniProt ID: P35372 Link_out
Gene: OPRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Greenwald MK, Johanson CE, Moody DE, Woods JH, Kilbourn MR, Koeppe RA, Schuster CR, Zubieta JK: Effects of buprenorphine maintenance dose on mu-opioid receptor availability, plasma concentrations, and antagonist blockade in heroin-dependent volunteers. Neuropsychopharmacology. 2003 Nov;28(11):2000-9. Pubmed
  2. Becker J, Schmidt P, Musshoff F, Fitzenreiter M, Madea B: MOR1 receptor mRNA expression in human brains of drug-related fatalities-a real-time PCR quantification. Forensic Sci Int. 2004 Feb 10;140(1):13-20. Pubmed
  3. Yao L, McFarland K, Fan P, Jiang Z, Inoue Y, Diamond I: Activator of G protein signaling 3 regulates opiate activation of protein kinase A signaling and relapse of heroin-seeking behavior. Proc Natl Acad Sci U S A. 2005 Jun 14;102(24):8746-51. Epub 2005 Jun 3. Pubmed
  4. Antonilli L, Petecchia E, Caprioli D, Badiani A, Nencini P: Effect of repeated administrations of heroin, naltrexone, methadone, and alcohol on morphine glucuronidation in the rat. Psychopharmacology (Berl). 2005 Oct;182(1):58-64. Epub 2005 Sep 29. Pubmed
  5. Choi HS, Kim CS, Hwang CK, Song KY, Wang W, Qiu Y, Law PY, Wei LN, Loh HH: The opioid ligand binding of human mu-opioid receptor is modulated by novel splice variants of the receptor. Biochem Biophys Res Commun. 2006 May 19;343(4):1132-40. Epub 2006 Mar 23. Pubmed

2. Kappa-type opioid receptor

Pharmacological action: unknown
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions

Organism class: human
UniProt ID: P41145 Link_out
Gene: OPRK1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Wee S, Koob GF: The role of the dynorphin-kappa opioid system in the reinforcing effects of drugs of abuse. Psychopharmacology (Berl). 2010 Jun;210(2):121-35. Epub 2010 Mar 30. Pubmed
  2. Klein G, Juni A, Arout CA, Waxman AR, Inturrisi CE, Kest B: Acute and chronic heroin dependence in mice: contribution of opioid and excitatory amino acid receptors. Eur J Pharmacol. 2008 May 31;586(1-3):179-88. Epub 2008 Feb 19. Pubmed

3. Delta-type opioid receptor

Pharmacological action: unknown
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins

Organism class: human
UniProt ID: P41143 Link_out
Gene: OPRD1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Klein G, Juni A, Arout CA, Waxman AR, Inturrisi CE, Kest B: Acute and chronic heroin dependence in mice: contribution of opioid and excitatory amino acid receptors. Eur J Pharmacol. 2008 May 31;586(1-3):179-88. Epub 2008 Feb 19. Pubmed
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  3. Kieffer BL, Gaveriaux-Ruff C: Exploring the opioid system by gene knockout. Prog Neurobiol. 2002 Apr;66(5):285-306. Pubmed
Comments
Drug created on July 31, 2007 07:09 / Updated on March 19, 2013 13:43