Tetramisole hydrochloride

• CAS: 5086-74-8
• Catalog Number: ACM5086748
• Category: Main Products
• Molecular Weight: 240.75
• Molecular Formula: C₁₁H₁₃ClN₂S
• Synonyms: Tetramisole hydrochloride; levamisole hydrochloride; 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride; citarin; l-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride; nilverom; anthelvet; nilverm; r8299; ripereol; Concurat; ripercol; bayer9051; orovermol; Tetramisole HCl; levamisole HCl
• IUPAC Name: Imidazo[2,1-b]thiazole,2,3,5,6-tetrahydro-6-phenyl-, hydrochloride (1:...
• Boiling Point: 344.4ºC at 760 mmHg
• Melting Point: 266-267ºC
• Flash Point: 162.1ºC
• Appearance: white to pale cream crystalline powder
• Exact Mass: 240.04900
• Hazard Statements: Xi:Irritant
• Safety Description: S26-S36
• Stability: Stable under normal temperatures and pressures.
• WGK Germany: 3

Case Study

Tetramisole Hydrochloride as a Versatile Organocatalyst for Asymmetric Michael Addition-Lactonization Reactions

Belmessieri, Dorine, et al. Journal of the American Chemical Society 133.8 (2011): 2714-2720.

This study examined the application of tetramisole hydrochloride as a chiral isothiourea-based organocatalyst in the stereoselective synthesis of lactones via intramolecular and intermolecular Michael addition-lactonization sequences.
· Intramolecular Michael addition-lactonization: In the intramolecular series, racemic conditions using Mukaiyama-type activation with DMAP or DHPB delivered the polycyclic lactone with excellent diastereocontrol (up to 99:1 dr); the isothiourea precatalyst tetramisole hydrochloride (4) provided high enantioselectivity (≈97% ee) and good diastereocontrol (≈95:5 → 99:1 dr) though initially required high loadings (50 mol %) to give useful yields; switching the activator to pivaloyl chloride allowed productive catalysis with 20 mol % tetramisole to afford the lactone in 62% yield with 99:1 dr and 97% ee, while a related isothiourea (5) was catalytically active but showed reduced stereocontrol.
· Intermolecular Michael addition-lactonization: For the more challenging intermolecular process, a chalcone acceptor failed to react under the tested conditions, but an α-keto-β,γ-unsaturated ester furnished the anti-dihydropyranone in 95:5 dr; tetramisole (4) promoted this transformation with promising selectivity (94:6 dr, 86% ee), whereas isothiourea 5 delivered higher enantiocontrol at room temperature (96:4 dr, 91% ee) and, upon cooling, up to 97% ee-additionally, catalyst 5 could be used at 2 mol% without loss of stereoselectivity, albeit with longer reaction times.

Evaluating the Impact of a Tetramisole Hydrochloride-Based Anthelmintic on Milk Production in Cattle with Trematode Infections

Kumar, Alok, et al. Society for Sci. Dev. in Agric. and Tech. 35-38 (2013).

A field evaluation assessed the impact of anthelmintic treatments on trematode infections and milk production in naturally infected cattle. One treatment group received NILZAN (a combined formulation of oxyclozanide + tetramisole hydrochloride, dosed at 10 mg/kg body weight orally), and two comparator groups received triclabendazole (FASINEX, 12 mg/kg p.o.) and closantel (EXINOT, 15 mg/kg p.o.). An infected, untreated group served as control. Outcomes recorded included faecal egg counts (FEC) over time and average milk yield measured before treatment and at 1, 2, 3, 4, 6 and 7 weeks post-treatment.
· Effective Parasite Clearance: The formulation achieved a 100% reduction in fecal egg counts for both Fasciola and amphistomes at 7 days post-treatment, confirming its efficacy against the target mixed infection.
· Significant Milk Yield Recovery: Following an initial slight dip in yield one week post-treatment, the milk production in the Tetramisole HCl/Oxyclozanide group showed a strong and sustained increase. Average yield rose from a pre-treatment baseline, recovering and surpassing initial levels in subsequent weeks, ultimately contributing to an overall positive production trend over the 7-week observation period.
· Positive Economic Outcome: Across the treated cohorts, the study reported a net profit of Rs. 84.24 per animal over the 7-week period. In contrast, untreated infected animals incurred a loss of Rs. 169.30 per animal over the same interval.

Custom Q&A

What is the molecular formula of Tetramisole hydrochloride?

The molecular formula of Tetramisole hydrochloride is C11H13ClN2S.

What are some synonyms for Tetramisole hydrochloride?

Some synonyms for Tetramisole hydrochloride include Anthelvet, Citarin, Concurat, and Nilverm.

What is the Chemical Safety of Tetramisole hydrochloride?

Tetramisole hydrochloride is classified as an irritant.

What is the CAS number for Tetramisole hydrochloride?

The CAS number for Tetramisole hydrochloride is 5086-74-8.

What is the 2D structure of Tetramisole hydrochloride?

The 2D structure of Tetramisole hydrochloride is not provided in the reference.

What is the 3D structure of Tetramisole hydrochloride?

The 3D structure of Tetramisole hydrochloride is not provided in the reference.

What are some other names for Tetramisole hydrochloride?

Some other names for Tetramisole hydrochloride include Tetramisole HCl, Citarin, Orovermol, and Spartakon.

What is the UNII number for Tetramisole hydrochloride?

The UNII number for Tetramisole hydrochloride is 0NDK265MCV.

What are the EINECS and CHEBI numbers for Tetramisole hydrochloride?

The EINECS number for Tetramisole hydrochloride is 225-799-5, and the CHEBI number is 9496.

What is the structural formula of Tetramisole hydrochloride?

The reference does not provide the structural formula of Tetramisole hydrochloride.

Synthetic Use

Upstream Synthesis Route 1

• 65329-72-8

• 5086-74-8

Reference: [1] Patent: US4087611, 1978, A,

Upstream Synthesis Route 2

• 65329-70-6

• 5086-74-8

Reference: [1] Patent: US4087611, 1978, A,

Upstream Synthesis Route 3

• 7440-44-0
• 65329-73-9

• 5086-74-8

Reference: [1] Patent: US4087611, 1978, A,

Downstream Synthesis Route 1

• 5086-74-8

• 20406-02-4

Reference: [1]Australian Journal of Chemistry,1968,vol. 21,p. 1557 - 1570

* For details of the synthesis route, please refer to the original source to ensure accuracy.