Acetylcholine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Acetylcholine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Acetylcholine?

The molecule Acetylcholine presents a molecular formula of C7H16NO2+ and its IUPAC name is 2-acetyloxyethyl(trimethyl)azanium.

Acetylcholine (ACh) is an organic molecule that acts as a neurotransmitter in the human body. ACh is produced by the body and participes in many important physiological processes, including muscle contraction, memory, and learning. It is also a key player in the autonomic nervous system, which controls involuntary bodily functions such as heart rate and digestion..

ACh is synthesized in the body from the amino acids choline and acetate. It is stored in nerve cells (neurons) and is released when the neuron is stimulated. Once released, ACh binds to receptors on target cells and triggers a response. The response can be either excitatory or inhibitory, depending on the type of receptor to which ACh binds..

ACh is broken down by the enzyme acetylcholinesterase (AChE), which belongs in high concentrations in the brain. AChE is responsible for clearing ACh from the synaptic cleft, the space between two neurons. This process is important in maintaining normal neurotransmission and preventing overstimulation of the nervous system..

ACh is an important molecule in the human body and plays a role in many physiological processes. It is also a target for drugs that are used to treat conditions such as Alzheimer’s disease, Parkinson’s disease, and other neurological disorders..

3D structure

Cartesian coordinates

Geometry of Acetylcholine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Acetylcholine OIPILFWXSMYKGL-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Acetylcholine

 

Molecule descriptors

 
IUPAC name2-acetyloxyethyl(trimethyl)azanium
InChI codeInChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1
InChI KeyOIPILFWXSMYKGL-UHFFFAOYSA-N
SMILESCC(=O)OCC[N+](C)(C)C

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (14C)-Acetylcholine
  • (14C)Acetylcholine
  • (2-Acetoxyethyl)trimethylammonium
  • (2-Acetoxyethyl)trimetilammonium
  • 14047-05-3
  • 2-(Acetyloxy)-N,N,N-trimethylethanaminium
  • 2-(Acetyloxy)-N,N,N-trimethylethanaminium labeled with carbon-14
  • 2-Acetoxy-N,N,N-trimethylethan-1-aminium
  • 2-acetoxyethyl(trimethyl)ammonium;bromide
  • 2-acetoxyethyl(trimethyl)ammonium;perchlorate
  • 2-acetyloxy-N,N,N-trimethylethanaminium
  • 2-acetyloxyethyl(trimethyl)azanium
  • 2-acetyloxyethyl-trimethylazanium
  • 2ha4
  • 2rin
  • 2xz5
  • 3rqw
  • 51-84-3
  • AB00053790-25
  • AB00053790_26
  • AB00053790_27
  • Acetyl choline cation
  • Acetyl choline ion
  • Acetylcholine
  • Acetylcholine cation
  • Acetylcholinium: acetyl-Choline
  • Acetylcholinum
  • Ach
  • Azetylcholin
  • BDBM10759
  • BRN 1764436
  • BSPBio_001792
  • C01996
  • COL Acetate
  • CS-0453239
  • Choline acetate
  • Choline acetate (ester)
  • DB03128
  • DivK1c_000686
  • Epitope ID:176773
  • Ethanaminium, 2-(acetyloxy)-N,N,N-trimethyl- (9CI)
  • Ethanaminium, 2-(acetyloxy)-N,N,N-trimethyl-, labeled with carbon-14
  • FT-0689161
  • GTPL294
  • GTPL8593
  • HMS2089A14
  • IDI1_000686
  • KBio1_000686
  • KBio2_000382
  • KBio2_002950
  • KBio2_005518
  • KBio3_001292
  • KBioGR_000552
  • KBioSS_000382
  • L000783
  • N9YNS0M02X
  • NCGC00018123-01
  • NCGC00018123-02
  • NCGC00018123-03
  • NCGC00018123-04
  • NCGC00018123-05
  • NCGC00021161-03
  • NCGC00021161-04
  • NCGC00163215-01
  • NINDS_000686
  • NSC-800293
  • NSC800293
  • O-Acetylcholine
  • Q180623
  • SBI-0051271.P003
  • [2-(acetyloxy)ethyl]trimethylazanium
  • [3H]acetylcholine
  • acetylcholine
  • cid_6060
  • ethanaminium, 2-(acetyloxy)-N,N,N-trimethyl
  • ethanaminium, 2-(acetyloxy)-N,N,N-trimethyl-
  • starbld0009701

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3079336
  • UNII-N9YNS0M02X
  • DTXSID8075334
  • CHEMBL667
  • CHEBI:15355
  • EINECS 200-128-9
  • SPBio_001196
  • SCHEMBL3216
  • Spectrum_000022
  • Spectrum2_001258
  • Spectrum3_000286
  • Spectrum4_000136
  • Spectrum5_000762

Physico-Chemical properties

IUPAC name2-acetyloxyethyl(trimethyl)azanium
Molecular formulaC7H16NO2+
Molecular weight146.207
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity39.42
LogP0.3
Topological polar surface area26.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.