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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:29:34 UTC
HMDB IDHMDB00895
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetylcholine
DescriptionAcetylcholine (ACh) is a neurotransmitter. Acetylcholine in vertebrates is the major transmitter at neuromuscular junctions, autonomic ganglia, parasympathetic effector junctions, a subset of sympathetic effector junctions, and at many sites in the central nervous system. Its physiological and pharmacological effects, metabolism, release, and receptors have been well documented in several species. ACh has been considered an important excitatory neurotransmitter in the carotid body (CB). Various nicotinic and muscarinic ACh receptors are present in both afferent nerve endings and glomus cells. Therefore, ACh can depolarize or hyperpolarize the cell membrane depending on the available receptor type in the vicinity. Binding of ACh to its receptor can create a wide variety of cellular responses including opening cation channels (nicotinic ACh receptor activation), releasing Ca2+ from intracellular storage sites (via muscarinic ACh receptors), and modulating activities of K+ and Ca2+ channels. Interactions between ACh and other neurotransmitters (dopamine, adenosine, nitric oxide) have been known, and they may induce complicated responses. Cholinergic biology in the CB differs among species and even within the same species due to different genetic composition. Development and environment influence cholinergic biology. Pharmacological data clearly indicate that both muscarinic and nicotinic acetylcholine receptors have a role in the encoding of new memories. Localized lesions and antagonist infusions demonstrate the anatomical locus of these cholinergic effects, and computational modeling links the function of cholinergic modulation to specific cellular effects within these regions. Acetylcholine has been shown to increase the strength of afferent input relative to feedback, to contribute to theta rhythm oscillations, activate intrinsic mechanisms for persistent spiking, and increase the modification of synapses. These effects might enhance different types of encoding in different cortical structures. In particular, the effects in entorhinal and perirhinal cortex and hippocampus might be important for encoding new episodic memories. The role of ACh in attention has been repeatedly demonstrated in several tasks. Acetylcholine is linked to response accuracy in voluntary and reflexive attention and also to response speed in reflexive attention. It is well known that those with Attention-deficit/hyperactivity disorders tend to be inaccurate and slow to respond. (PMID: 17284361 , 17011181 , 15556286 ).
Structure
Thumb
Synonyms
  1. Acetyl choline ion
  2. Acetylcholine cation
  3. Acetylcholinium: acetyl-Choline
  4. ACh
  5. Choline acetate
  6. Choline acetate (ester)
  7. O-Acetylcholine
Chemical FormulaC7H16NO2
Average Molecular Weight146.2074
Monoisotopic Molecular Weight146.118103761
IUPAC Name[2-(acetyloxy)ethyl]trimethylazanium
Traditional IUPAC Nameacetylcholine
CAS Registry Number51-84-3
SMILES
CC(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1
InChI KeyOIPILFWXSMYKGL-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlcohols and Polyols
Sub ClassCholines
Other Descriptors
  • Acetylcholine(KEGG)
  • a small molecule(Cyc)
  • acetate ester(ChEBI)
  • acylcholine(ChEBI)
Substituents
  • Carboxylic Acid Ester
  • Quaternary Ammonium Salt
Direct ParentCholines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycerophospholipid metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP-2.9ALOGPS
logP-4.2ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.35ChemAxon
Polarizability16.83ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Nucleus
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Adipose Tissue
  • Adrenal Medulla
  • Bladder
  • Brain
  • Fibroblasts
  • Intestine
  • Kidney
  • Lung
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Skin
  • Spleen
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Phospholipid BiosynthesisSMP00025map00564
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.034 +/- 0.009 uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.01 +/- 0.005 uMAdult (>18 years old)Not SpecifiedAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.016 +/- 0.007 uMAdult (>18 years old)Not SpecifiedVascular dementia details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Jia JP, Jia JM, Zhou WD, Xu M, Chu CB, Yan X, Sun YX: Differential acetylcholine and choline concentrations in the cerebrospinal fluid of patients with Alzheimer's disease and vascular dementia. Chin Med J (Engl). 2004 Aug;117(8):1161-4. Pubmed: 15361288
Multi-infarct dementia
  1. Jia JP, Jia JM, Zhou WD, Xu M, Chu CB, Yan X, Sun YX: Differential acetylcholine and choline concentrations in the cerebrospinal fluid of patients with Alzheimer's disease and vascular dementia. Chin Med J (Engl). 2004 Aug;117(8):1161-4. Pubmed: 15361288
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012191
KNApSAcK IDNot Available
Chemspider ID182
KEGG Compound IDC01996
BioCyc IDACETYLCHOLINE
BiGG ID38868
Wikipedia LinkAcetylcholine
NuGOwiki LinkHMDB00895
Metagene LinkHMDB00895
METLIN ID57
PubChem Compound187
PDB IDACH
ChEBI ID15355
References
Synthesis ReferenceSzutowicz, Andrzej. Acetylcholine synthesis in synaptosomes. Postepy Biochemii (1979), 25(1), 59-84.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nguyen VT, Ndoye A, Hall LL, Zia S, Arredondo J, Chernyavsky AI, Kist DA, Zelickson BD, Lawry MA, Grando SA: Programmed cell death of keratinocytes culminates in apoptotic secretion of a humectant upon secretagogue action of acetylcholine. J Cell Sci. 2001 Mar;114(Pt 6):1189-204. Pubmed: 11228162
  2. Chia S, Megson IL, Ludlam CA, Fox KA, Newby DE: Preserved endothelial vasomotion and fibrinolytic function in patients with acute stent thrombosis or in-stent restenosis. Thromb Res. 2003;111(6):343-9. Pubmed: 14698651
  3. Grando SA, Kist DA, Qi M, Dahl MV: Human keratinocytes synthesize, secrete, and degrade acetylcholine. J Invest Dermatol. 1993 Jul;101(1):32-6. Pubmed: 8331294
  4. Beilin B, Bessler H, Papismedov L, Weinstock M, Shavit Y: Continuous physostigmine combined with morphine-based patient-controlled analgesia in the postoperative period. Acta Anaesthesiol Scand. 2005 Jan;49(1):78-84. Pubmed: 15675987
  5. Tao J, Jin YF, Yang Z, Wang LC, Gao XR, Lui L, Ma H: Reduced arterial elasticity is associated with endothelial dysfunction in persons of advancing age: comparative study of noninvasive pulse wave analysis and laser Doppler blood flow measurement. Am J Hypertens. 2004 Aug;17(8):654-9. Pubmed: 15288882
  6. Jiang JL, Jiang DJ, Tang YH, Li NS, Deng HW, Li YJ: Effect of simvastatin on endothelium-dependent vaso-relaxation and endogenous nitric oxide synthase inhibitor. Acta Pharmacol Sin. 2004 Jul;25(7):893-901. Pubmed: 15210062
  7. Haug KH, Bogen IL, Osmundsen H, Walaas I, Fonnum F: Effects on cholinergic markers in rat brain and blood after short and prolonged administration of donepezil. Neurochem Res. 2005 Dec;30(12):1511-20. Pubmed: 16362770
  8. Katoh H, Shimada T, Inoue S, Takahashi N, Shimizu H, Ohta Y, Nakamura K, Murakami Y, Ishibashi Y, Matsumori A: Reduced high serum hepatocyte growth factor levels after successful cardioversion in patients with atrial fibrillation. Clin Exp Pharmacol Physiol. 2004 Mar;31(3):145-51. Pubmed: 15008956
  9. Main C, Blennerhassett P, Collins SM: Human recombinant interleukin 1 beta suppresses acetylcholine release from rat myenteric plexus. Gastroenterology. 1993 Jun;104(6):1648-54. Pubmed: 8500722
  10. Ikarashi Y, Harigaya Y, Tomidokoro Y, Kanai M, Ikeda M, Matsubara E, Kawarabayashi T, Kuribara H, Younkin SG, Maruyama Y, Shoji M: Decreased level of brain acetylcholine and memory disturbance in APPsw mice. Neurobiol Aging. 2004 Apr;25(4):483-90. Pubmed: 15013569
  11. Katz SD, Krum H: Acetylcholine-mediated vasodilation in the forearm circulation of patients with heart failure: indirect evidence for the role of endothelium-derived hyperpolarizing factor. Am J Cardiol. 2001 May 1;87(9):1089-92. Pubmed: 11348607
  12. Hanna ST, Cao K, Wang R: Interaction of acetylcholine with Kir6.1 channels heterologously expressed in human embryonic kidney cells. Eur J Pharmacol. 2005 May 16;515(1-3):34-42. Pubmed: 15894309
  13. Greig NH, Utsuki T, Ingram DK, Wang Y, Pepeu G, Scali C, Yu QS, Mamczarz J, Holloway HW, Giordano T, Chen D, Furukawa K, Sambamurti K, Brossi A, Lahiri DK: Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer beta-amyloid peptide in rodent. Proc Natl Acad Sci U S A. 2005 Nov 22;102(47):17213-8. Epub 2005 Nov 7. Pubmed: 16275899
  14. Shirahata M, Balbir A, Otsubo T, Fitzgerald RS: Role of acetylcholine in neurotransmission of the carotid body. Respir Physiol Neurobiol. 2007 Jul 1;157(1):93-105. Epub 2007 Jan 11. Pubmed: 17284361
  15. Hasselmo ME: The role of acetylcholine in learning and memory. Curr Opin Neurobiol. 2006 Dec;16(6):710-5. Epub 2006 Sep 29. Pubmed: 17011181
  16. Beane M, Marrocco RT: Norepinephrine and acetylcholine mediation of the components of reflexive attention: implications for attention deficit disorders. Prog Neurobiol. 2004 Oct;74(3):167-81. Pubmed: 15556286

Enzymes

General function:
Involved in acyltransferase activity
Specific function:
Catalyzes the reversible synthesis of acetylcholine (ACh) from acetyl CoA and choline at cholinergic synapses.
Gene Name:
CHAT
Uniprot ID:
P28329
Molecular weight:
70425.285
Reactions
Acetyl-CoA + Choline → Coenzyme A + Acetylcholine details
General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525
Reactions
Acetylcholine + Water → Choline + Acetic aciddetails
General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575