Metoclopramide (C14H22ClN3O2): structure, properties and hazards

Names and identifiers

IUPAC name: 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide
Synonyms: Reglan, prokinetic, antiemetic
+ 38 more
Methochlopramide, Metochlopramide, Reliveran, Metaclopramide, Elieten, Terperan, Metoclopramida, 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide, Metoclopramidum, 2-Methoxy-5-chloroprocainamide, 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide, 5-Chloro-2-methoxyprocainamide, Methoxyclopramide, 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-o-anisamide, Benzamide, 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxy-, DTXSID6045169, 4-Amino-5-chloro-2-methoxy-N-(beta-diethylaminoethyl)benzamide, N-(Diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide, L4YEB44I46, Benzamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxy-, 4-amino-5-chloro-N-(2-diethylaminoethyl)-2-methoxybenzamide, DTXCID4025169, 2-methoxy-4-amino-5-chloro-N,N-(dimethylaminoethyl)benzamide, CHEBI:107736, RefChem:6035, A03FA01, 206-662-9, Primperan, Metaclopromide, Methoclopramide, Plasil (pharmaceutical), Metoclopramidum [INN-Latin], Metoclopramida [INN-Spanish], Maxeran, Metocobil, DEL 1267, MFCD00211338, CLOPRA-"YELLOW"
Molecular formula: C₁₄H₂₂ClN₃O₂
Empirical formula: C₁₄H₂₂ClN₃O₂
Molecular weight: 299.79 g/mol
Exact mass: 299.14005
CAS number: 364-62-5
PubChem CID: 4168
Canonical SMILES: CCN(CC)CCNC(=O)C1=CC(=C(C=C1OC)N)Cl
Isomeric SMILES: CCN(CC)CCNC(=O)C1=CC(=C(C=C1OC)N)Cl
InChI: InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)
InChIKey: TTWJBBZEZQICBI-UHFFFAOYSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Physical properties

pKa: pka = 9.27[1]

Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.

Calculated

Heavy atoms: 20
Rings: 1
Aromatic rings: 1
Fraction sp³ carbons (Fsp3): 0.5
H-bond donors: 2
H-bond acceptors: 4
Rotatable bonds: 7
TPSA (Å²): 67.6
Formal charge: 0
XLogP3: 2.6 PubChem
Complexity: 300 PubChem
Stereocenters: None
Double-bond geometry: None specified
Point group: C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

C56.09%
H7.40%
Cl11.83%
N14.02%
O10.67%

Isotope pattern

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P: 2 Crippen (Wildman and Crippen 1999)
log S (water solubility): -2.72 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 2.11 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 299.8
log P ≤ 5 (Crippen): 2
H-bond donors ≤ 5: 2
H-bond acceptors ≤ 10: 4

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Danger

Most widely reported: 51 company reports to ECHA. Source [2].

Harmful or irritant
Health hazard

H302Harmful if swallowed
H362May cause harm to breast-fed children (76.5% of reports)
H370Causes damage to organs (19.6% of reports)

Precautionary statements: P203, P260, P263, P264, P270, P301+P317, P308+P316, P318, P321, P330, P405, P501

Storage

Metoclopramide hydrochloride tablets, injection, and oral solution should be stored at controlled room temperature between 20-25 °C. Metoclopramide hydrochloride tablets and metoclopramide hydrochloride oral solution should be stored in tight, light-resistant containers (ie, amber glass bottles).[1]
Store in tight, light-resistant container as defined in the usp-nf. This material should be handled and stored per label instructions to ensure product integrity.[1]

Incompatibilities

(incompattable with) strong alkalis, strong oxidizing agents.[1]

Safety data sheets on the supplier’s page: eMolecules, Chem-Space.com Database, TimTec.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

[1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
[2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
[3]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
[4]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
[5]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
[6]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[7]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
·Literature on PubChem

Data last updated 2026-10-14.