Chemicals and Drugs

Cyclic AMP

An adenine nucleotide containing one phosphate group which is esterified to both the 3'- and 5'-positions of the sugar moiety. It is a second messenger and a key intracellular regulator, functioning as a mediator of activity for a number of hormones, including epinephrine, glucagon, and ACTH.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

An adenine nucleotide containing one phosphate group which is esterified to both the 3'- and 5'-positions of the sugar moiety. It is a second messenger and a key intracellular regulator, functioning as a mediator of activity for a number of hormones, including epinephrine, glucagon, and ACTH.

Chemical Identity

Chemical Information

Molecular Formula
C10H12N5O6P
Molecular Weight
329.21 g/mol
CAS Registry No.
60-92-4
IUPAC Name
(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
InChIKey
IVOMOUWHDPKRLL-KQYNXXCUSA-N
SMILES
C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)O
MeSH Unique ID
D000242
Source
PubChem CID 6076

MeSH Record

Classification

Broader headings

Narrower headings

Related Concepts

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MeSH Record

See Also

MeSH Record

Synonyms

17 entry terms
  • Adenosine Cyclic 3',5'-Monophosphate
  • Adenosine Cyclic 3,5 Monophosphate
  • Adenosine Cyclic Monophosphate
  • Adenosine Cyclic-3',5'-Monophosphate
  • 3',5'-Monophosphate, Adenosine Cyclic
  • AMP, Cyclic
  • Adenosine Cyclic 3',5' Monophosphate
  • Cyclic 3',5'-Monophosphate, Adenosine
  • Cyclic Monophosphate, Adenosine
  • Cyclic-3',5'-Monophosphate, Adenosine
  • Monophosphate, Adenosine Cyclic
  • Cyclic AMP, (R)-Isomer
  • Cyclic AMP, Disodium Salt
  • Cyclic AMP, Monoammonium Salt
  • Cyclic AMP, Monopotassium Salt
  • Cyclic AMP, Monosodium Salt
  • Cyclic AMP, Sodium Salt

MeSH Record

Aspects Covered

29 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, deficiency, economics, genetics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, physiology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

94; was ADENOSINE CYCLIC MONOPHOSPHATE 1980-93, was ADENOSINE CYCLIC-3',5'-MONOPHOSPHATE 1978-79, was ADENOSINE CYCLIC 3',5' MONOPHOSPHATE 1968-77 (Prov 1968-71); CYCLIC AMP was see ADENOSINE CYCLIC MONOPHOSPHATE 1976-93; ADENOSINE CYCLIC 2',3'-MONOPHOSPHATE was see ADENOSINE CYCLIC MONOPHOSPHATE 1980-93

MeSH Record

Previous Indexing

  • Adenine Nucleotides (1966-1968)

MeSH Hierarchy

Tree Numbers

  1. D03w.633.100.759.646.138.395w
  2. D13.695w.462w.200w
  3. D13.695w.667.138.395w
  4. D13.695w.827w.068.395w

MeSH Record

NLM Classification

QU 57

AMA Style

References

  1. National Library of Medicine. Cyclic AMP. Medical Subject Headings (MeSH). 2026. Unique ID D000242. http://id.nlm.nih.gov/mesh/2026/D000242
  2. Cyclic AMP. In: Wikipedia. https://en.wikipedia.org/wiki/Cyclic_adenosine_monophosphate
  3. Cyclic AMP. In: Wikidata. https://www.wikidata.org/wiki/Q210041
  4. Cyclic AMP. In: PubChem Compound. CID 6076. https://pubchem.ncbi.nlm.nih.gov/compound/6076