Hemicholinium 3

Modify Date: 2025-08-23 12:05:29

Hemicholinium 3 structure	Common Name	Hemicholinium 3
	CAS Number	312-45-8	Molecular Weight	574.35
	Density	N/A	Boiling Point	N/A
	Molecular Formula	C₂₄H₃₄Br₂N₂O₄	Melting Point	180 °C
	MSDS	Chinese USA	Flash Point	N/A
	Symbol	GHS06	Signal Word	Danger

Use of Hemicholinium 3

Hemicholinium 3 is a competitive inhibitor of the high affinity choline transporter (HACU) with a Ki value of 25 nM. Hemicholinium 3, a neuromuscular blocking agent which inhibits the synthesis and the release of acetylcholine (ACh)[1]. Hemicholinium 3 inhibits the Epibatidine-evoked contraction and [3H]acetylcholine release with IC50s of 897 nM and 693 nM, respectively[2].

Name	2-[4-[4-(2-hydroxy-4,4-dimethylmorpholin-4-ium-2-yl)phenyl]phenyl]-4,4-dimethylmorpholin-4-ium-2-ol,dibromide
Synonym	More Synonyms

Description	Hemicholinium 3 is a competitive inhibitor of the high affinity choline transporter (HACU) with a Ki value of 25 nM. Hemicholinium 3, a neuromuscular blocking agent which inhibits the synthesis and the release of acetylcholine (ACh)[1]. Hemicholinium 3 inhibits the Epibatidine-evoked contraction and [3H]acetylcholine release with IC50s of 897 nM and 693 nM, respectively[2].
Related Catalog	Research Areas >> Neurological Disease Signaling Pathways >> Neuronal Signaling >> AChE
In Vitro	Hemicholinium 3 (HC-3) inhibits the presynaptic nicotinic acetylcholine receptors of myenteric neurons. HC-3 inhibits nAChRs located on the terminal region of myenteric neurons of guinea-pig longitudinal muscle strip preparation[2]. Hemicholinium 3 (HC-3) inhibits[3H]choline uptake with the Ki value of 13.3 μM in NCI-H69 cells[3]. HC-3 (1 mM) significantly inhibits cell viability and increases caspase-3/7 activity in NCI-H69 cells[3]. Hemicholinium 3 (Hemicholinium-3) inhibits sodium dependent high affinity choline uptake (IC50=18 nM)[4]. In vivo： Cell Viability Assay[3] Cell Line: The human small cell lung carcinoma cell line NCI-H69 Concentration: 1 mM Incubation Time: Added every day for 2 days. Result: Markedly inhibited cell viability.
In Vivo	Hemicholinium-3 impairs spatial learning. HC-3 (2.5, 5.0 μg/rat/ICV; 1 h before training) dose dependently impairs spatial learning[5].
References	[1]. PATRICE GUYENET, et al. Inhibition by Hemicholinium-3 of [¹⁴C] Acetylcholine Synthesis and [³H] Choline High-Affinity Uptake in Rat Striatal Synaptosomes.Molecular Pharmacology September 1973, 9 (5) 630-639. [2]. Péter Mandl, et al. Inhibitory effect of hemicholinium-3 on presynaptic nicotinic acetylcholine receptors located on the terminal region of myenteric motoneurons. Neurochem Int. 2006 Sep;49(4):327-33. [3]. Masato Inazu, et al. Functional expression of choline transporter-like protein 1 (CTL1) in small cell lung carcinoma cells: a target molecule for lung cancer therapy. Pharmacol Res. 2013 Oct;76:119-31. [4]. T K Chatterjee, et al. Methylpiperidine analog of hemicholinium-3: a selective, high affinity non-competitive inhibitor of sodium dependent choline uptake system. Eur J Pharmacol. 1988 May 10;149(3):241-8. [5]. J J Hagan, et al. Hemicholinium-3 impairs spatial learning and the deficit is reversed by cholinomimetics. Psychopharmacology (Berl). 1989;98(3):347-56.

Melting Point	180 °C
Molecular Formula	C₂₄H₃₄Br₂N₂O₄
Molecular Weight	574.35
Exact Mass	572.08900
PSA	58.92000
InChIKey	OPYKHUMNFAMIBL-UHFFFAOYSA-L
SMILES	C[N+]1(C)CCOC(O)(c2ccc(-c3ccc(C4(O)C[N+](C)(C)CCO4)cc3)cc2)C1.[Br-].[Br-]

Hemicholinium 3 MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QF2450000

CHEMICAL NAME :: Morpholinium, 2,2'-(4,4'-biphenylylene)bis(2-hydroxy-4,4-dimethyl-, dibromide

CAS REGISTRY NUMBER :: 312-45-8

LAST UPDATED :: 199701

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C24-H34-N2-O4.2Br

MOLECULAR WEIGHT :: 574.42

WISWESSER LINE NOTATION :: T6K DOTJ A1 A1 CQ CR DR D- CT6K DOTJ A1 A1 CQ &Q 2 &E

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 160 ug/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: EJPHAZ European Journal of Pharmacology. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1967- Volume(issue)/page/year: 33,145,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 450 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IRNEAE International Review of Neurobiology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 2,77,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 46 ug/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: EJPHAZ European Journal of Pharmacology. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1967- Volume(issue)/page/year: 33,145,1975

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 150 ug/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 152,253,1964

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 80 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 27,666,1974

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IRNEAE International Review of Neurobiology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 2,77,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 750 ug/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 4,505,1961

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 300 ug/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 4,505,1961

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 250 ug/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - tremor Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 119,20,1959

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 300 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IRNEAE International Review of Neurobiology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 2,77,1960

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301 + H311 + H331-H315-H319-H335
Precautionary Statements	P261-P280-P301 + P310-P305 + P351 + P338-P311
Personal Protective Equipment	Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes	T: Toxic;
Risk Phrases	23/24/25-36/37/38
Safety Phrases	S26;S45;S36/S37/S39
RIDADR	UN 2811 6.1/PG 2
RTECS	QF2450000
Packaging Group	III
Hazard Class	6.1(b)

2-(Dimethylamin...

CAS#:108-01-0

4,4'-Bis(2-brom...

CAS#:4072-67-7

~92%

Hemicholinium 3

CAS#:312-45-8

Literature: Zheng, Qi-Huang; Gao, Mingzhang; Mock, Bruce H.; Wang, Shuyan; Hara, Toshihiko; Nazih, Rachid; Miller, Michael A.; Receveur, Tim J.; Lopshire, John C.; Groh, William J.; Zipes, Douglas P.; Hutchins, Gary D.; DeGrado, Timothy R. Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 8 p. 2220 - 2224

Precursor 2
CAS#:108-01-0 2-(Dimethylamin... CAS#:4072-67-7 4,4'-Bis(2-brom...
DownStream 0

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Hemicholinium dibromide

HC-3

HEMICHOLINIUM 3

EINECS 206-227-3

Hemicholinium 3 dibromide

Hemicholinium bromide

Hemicholinium-3 bromide

Hemicholinium-3

MFCD00011978

hemicholinium

Hemicholine

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