Levamisol hydrochloride - analytical standard , Nicotinic acetylcholine receptor alpha subunit agonist, CAS No.16595-80-5, Nicotinic acetylcholine receptor alpha subunit agonist

CAS: 16595-80-5 Cat. No.: L114327 Molecular Weight: 240.75 EC Number: 240-654-6
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GRADE & PURITY Analytical standard ? Analytical standard — certified-purity material for quantitative calibration. Use to prepare calibration standards and validate analytical methods.
Synonyms
(-)-Tetramisole hydrochloride | BMK1-H6 | HMS1568F05 | Levomysol hydrochloride | EINECS 240-654-6 | Ergamisol (TN) (Janssen) | Levamisole HCl | Levasole Soluble Pig Wormer | R 12564 | Citarin L | Levamisole hydrochloride [USAN:USP] | LEVAMISOLE HYDROCHLOR
Storage
Room temperature
Shipped In
Normal
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Size
Status
Price
Qty
250mg
L114327-250mg
3

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$151.90
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Why this grade

analytical standard Analytical standard for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Room temperature Ships Normal Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 22 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Specifications

Synonyms
(-)-Tetramisole hydrochloride | BMK1-H6 | HMS1568F05 | Levomysol hydrochloride | EINECS 240-654-6 | Ergamisol (TN) (Janssen) | Levamisole HCl | Levasole Soluble Pig Wormer | R 12564 | Citarin L | Levamisole hydrochloride [USAN:USP] | LEVAMISOLE HYDROCHLOR
Specifications & Purity
analytical standard
Biochemical and Physiological Mechanisms
Shows both immunostimulant and immunosuppressant effects, depending on several controllable factors.Very effective in treatment of ascariasis (hookworm infestation). Useful in chemotherapy of colorectal cancers, possibly due to its stimulation of IL-1 pro
Storage
Room temperature
Shipped In
Normal
Grade
Analytical standard
Action Type
AGONIST
Mechanism of action
Nicotinic acetylcholine receptor alpha subunit agonist
Names and Identifiers
Canonical SmilesC1CSC2=NC(CN21)C3=CC=CC=C3.Cl
IUPAC Name(6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole;hydrochloride
InChIKeyLAZPBGZRMVRFKY-HNCPQSOCSA-N
INCHI1S/C11H12N2S.ClH/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10;/h1-5,10H,6-8H2;1H/t10-;/m1./s1
Isomeric SMILES C1CSC2=N[C@H](CN21)C3=CC=CC=C3.Cl
UN Number 2811
Packing Group III
Molecular Weight 240.75
Reaxy-Rn 4358987
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4358987&ln=

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

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✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

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📊 Datasheet

Quick-reference summary of product specifications and applications.

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🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

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Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassImidazothiazoles
SubclassNot available
Intermediate Tree Nodes Not available
Direct ParentImidazothiazoles
Alternative Parents Benzene and substituted derivatives  Thiazolidines  Imidazolines  Isothioureas  Propargyl-type 1,3-dipolar organic compounds  Carboximidamides  Azacyclic compounds  Organopnictogen compounds  Hydrochlorides  Hydrocarbon derivatives  
Molecular FrameworkAromatic heteropolycyclic compounds
Substituents Imidazothiazole - Monocyclic benzene moiety - Benzenoid - 2-imidazoline - Thiazolidine - Isothiourea - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Azacycle - Organic 1,3-dipolar compound - Hydrochloride - Organonitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as imidazothiazoles. These are organic polycyclic compounds containing an imidazole ring fused to a thiazole ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Thiazole is a 6-membered ring that contains both sulfur and nitrogen.
External Descriptors organic molecular entity
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
A498 (42825 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHN (49357 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAKI-1 (44928 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCRF-CEM (65223 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
COLO 205 (50209 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-29 (80576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KM12 (47707 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
M14 (47487 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MOLT-4 (49676 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-3 (48710 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-4 (44535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-5 (45555 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-8 (47708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RXF 393 (41971 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-295 (48000 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-2 (46422 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-28 (48833 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-5 (47095 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-OV-3 (52876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SN12C (47755 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SNB-19 (46794 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U-251 (51189 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UACC-257 (46019 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UACC-62 (47335 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UO-31 (46270 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
786-0 (47912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI/ADR-RES (33767 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
T47D (39041 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EKVX (44102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H322M (45589 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCC 2998 (41480 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HOP-92 (41141 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H460 (60772 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-268 (49410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IGROV-1 (47897 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LOX IMVI (44321 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HOP-62 (47048 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-435 (38290 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-N (28205 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Malme-3M (44254 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SNB-75 (44215 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H226 (44470 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Associated Targets(non-human)
Iap Intestinal alkaline phosphatase (419 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FTL Ferritin light chain (43324 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mechanisms of Action
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Find and download the COA for your product by matching the lot number on the packaging.

1 results found

Lot NumberCertificate TypeDateItem
G1507195Certificate of AnalysisMay 20, 2026 L114327
Chemical and Physical Properties
Specific Rotation[α]-126 ° (C=1, H2O)
Melt Point(°C)228-230°C
Molecular Weight240.750 g/mol
XLogP3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass240.049 Da
Monoisotopic Mass240.049 Da
Topological Polar Surface Area40.900 Ų
Heavy Atom Count15
Formal Charge0
Complexity246.000
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count2
Documents & Articles
Citations of This Product
References
1. Shuna Chen, Jiaxin Kang, Huanqing Zhu, Ziyi Han, Leyu Wang, Kaixi Wang, Junsheng Liu, Yuanyuan Wu, Puming He, Youying Tu, Bo Li.  (2023)  Tea seed saponins ameliorate cyclophosphamide-induced intestinal injury, immune disorder and gut microbial dysbiosis in mice.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2023.103504]
2. Anqi Xie, Hao Wan, Lei Feng, Boyun Yang, Yiqun Wan.  (2023)  Protective Effect of Anoectochilus formosanus Polysaccharide against Cyclophosphamide-Induced Immunosuppression in BALB/c Mice.  Foods,  12  (9): (1910).  [PMID:37174447] [10.3390/foods12091910]
3. Han Mengyao, Zhang Zhongshan, Li Xinyue, Tong Haibin, Xu Zhiguo, Ding Zikang, Yang Anquan, Xie Min, Wang Xiaomei.  (2022)  Effects of collagen peptides from Micropterus salmoides skin on oxidative damage induced by cyclophosphamide in mice.  Frontiers in Nutrition,      [PMID:36407538] [10.3389/fnut.2022.1037212]
4. Chao Han, Ying Wang, Ruiying Liu, Beibei Ran, Weidong Li.  (2022)  Structural characterization and protective effect of Lonicerae flos polysaccharide on cyclophosphamide-induced immunosuppression in mice.  ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY,      [PMID:34999342] [10.1016/j.ecoenv.2022.113174]
5. Pengshuai Zhang, Yameng Wan, Chi Zhang, Rui Zhao, Jiao Sha, Yu Li, Tao Li, Baozeng Ren.  (2019)  Solubility and mixing thermodynamic properties of levamisole hydrochloride in twelve pure solvents at various temperatures.  JOURNAL OF CHEMICAL THERMODYNAMICS,      [PMID:] [10.1016/j.jct.2019.105882]
6. Huiting Fang, Huizhen Li, Yang Chen, Xiaoming Liu, Jianxin Zhao, Paul Ross, Catherine Stanton, Wei Chen, Bo Yang.  (2024)  Bifidobacterium breve CCFM1310 enhances immunity in immunosuppressed mice via modulating immune response and gut microbiota.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2024.104058]
7. Yahui Jia, Zhiqiang Zhang, Siming Zhang, Xia Ma, Yuan Ruan, Bingji Ma, Li Wang.  (2024)  Effects of polysaccharide from hot-compressed steamed Rehmannia glutinosa on the immune system and gut microbiota in an immunosuppressed mice model.  INTERNATIONAL IMMUNOPHARMACOLOGY,      [PMID:39303540] [10.1016/j.intimp.2024.113202]
8. Ying Yang, Mengfan Luo, Wanyi Zhou, Wenyang Tao, Jingrui Li, Jianrong Xing, Quanqin Tan, Yuxing Guo.  (2024)  Lactiplantibacillus plantarum YY-112 ameliorates mouse immunosuppression by enhancing B/T-cell activation and maintaining Th1/Th2 homeostasis.  Food Frontiers,      [PMID:] [10.1002/fft2.477]
9. Weiguang Luo, Xiuwei Li, Chenxi Zhang, Kai Shen, Mengxue Li, Yan Zhuang, Jinhai Huo, Weiming Wang.  (2025)  Physicochemical characterization and protective effects of raw and nine-steamed Polygonatum cyrtonema polysaccharides on cyclophosphamide-induced immunosuppression in mice.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40068755] [10.1016/j.ijbiomac.2025.141911]
10. Lin Chen, Qihong Jiang, Shiwei Yao, Chenkai Jiang, Hongling Lu, Wenjun Hu, Shaofang Yu, Mingqian Li, Yongcai Feng, Chin Ping Tan, Xingwei Xiang, Guoxin Shen.  (2024)  Sciadonic acid ameliorates cyclophosphamide-induced immunosuppression by modulating the immune response and altering the gut microbiota.  JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE,      [PMID:38264943] [10.1002/jsfa.13271]
11. Xinru Du, Yongheng Yan, Yufeng Dai, Ruijie Xu.  (2024)  Yogurt Alleviates Cyclophosphamide-Induced Immunosuppression in Mice through D-Lactate.  Nutrients,  16  (9): (1395).  [PMID:38732641] [10.3390/nu16091395]
12. Mengling Zhong, Mingmei Feng, Xinlin Chen, Yuxin Zhang, Yupeng Wang, Peizhi Yuan, Tianyao Zhang, Zhipeng Han, Chenglun Tang, Qi Zhang, Yang Sun.  (2025)  Cordycepin attenuated cyclophosphamide (CTX)-induced immunosuppression in mice via EGFR/Nrf2 antioxidant signaling pathway.  INTERNATIONAL IMMUNOPHARMACOLOGY,      [PMID:40695148] [10.1016/j.intimp.2025.115235]
13. Xian-Yi Jin, Jia Luo, Hang Cong, Jiang-Lin Zhao.  (2025)  Synergic Electrochemiluminescence System with Hemicucurbituril-Based CQDs and a Chiral Macrocycle for Recognition Toward Levamisole Hydrochloride.  ChemistrySelect,  10  (28): (e00823).  [PMID:] [10.1002/slct.202500823]
14. Ming Zhao, Huiyan Huang, Bowen Li, Yu Pan, Chuankai Wang, Wanjia Du, Wenliang Wang, Yansheng Wang, Xue Mao, Xianghui Kong.  (2025)  Preparation of Auricularia auricula-Derived Immune Modulators and Alleviation of Cyclophosphamide-Induced Immune Suppression and Intestinal Microbiota Dysbiosis in Mice.  Life-Basel,  15  (8): (1236).  [PMID:40868884] [10.3390/life15081236]
15. Pengshuai Zhang, Jiao Sha, Yameng Wan, Chi Zhang, Tao Li, Baozeng Ren.  (2019)  Apparent thermodynamic analysis and the dissolution behavior of levamisole hydrochloride in three binary solvent mixtures.  THERMOCHIMICA ACTA,      [PMID:] [10.1016/j.tca.2019.178375]
16. Song Wang, Chenyu Jiang, Shitong Yu, Qianru Fan, Kai Yang, Jianqin Huang, Yan Li.  (2025)  Hickory nut polyphenols enhance oxidative stress resilience and improve the longevity of Caenorhabditis elegans through modulating DAF-16/DAF-2 insulin/IGF-1 signaling.  PHYTOMEDICINE,      [PMID:40466506] [10.1016/j.phymed.2025.156918]
17. Aijing Jia, Yucong Xu, Chaonan Sun, Hongwei Luan, Zhiteng Liu, Ying Bu, Wenhui Zhu, Xuepeng Li.  (2025)  Identification and molecular mechanisms of novel antioxidant peptides from Manila clam hydrolysate: Caenorhabditis elegans model, molecular simulations, and quantum chemistry.  FOOD CHEMISTRY,      [PMID:40516351] [10.1016/j.foodchem.2025.145079]
18. Li Wang, Yupeng Yang, Xuelian Tang, Chunnan Wen, Zhiqiang Zhang, Xia Ma, Bingji Ma.  (2025)  Effects of polysaccharides from Stropharia rugosoannulata on cyclophosphamide-induced immunosuppression and hepatic injury in mice.  JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE,      [PMID:41195471] [10.1002/jsfa.70295]
19. Ji Zhang, Xueting Guan, Jianmei Zhang, Weicheng Hu, Chuanling Si, Honggang Wang, Ting Shen.  (2025)  Polysaccharides from lotus root residue alleviate cyclophosphamide-induced immunosuppression in mice.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2025.122303]
20. Caihong Chen, Haiyan Wu, Guanchao Zheng, Limin Lu, Zhijun Tan.  (2025)  Enhanced Toxicity of Diol-Estered Diarrhetic Shellfish Toxins Across Trophic Levels: Evidence from Caenorhabditis elegans and Mytilus galloprovincialis.  Marine Drugs,  23  (12): (459).  [PMID:41440892] [10.3390/md23120459]
21. Shiqiong Xiang, Yang Chen, Jiayue Xia, Guiju Sun.  (2025)  Purification, Structural Characterization, and Immunomodulatory Activities of a Glucan from Morchella sextelata.  Foods,  15  (1): (105).  [PMID:41517171] [10.3390/foods15010105]
22. Bo Li, Lin Zhang, Ding-Tao Wu, Qin Yuan, Shengpeng Wang, Mao-Ling Tan, Mei-Lin Feng, Yi-Chen Hu, Liang Zou, Zi-Peng Wang, Ya-Nan Cao, Jing-Wei Huang.  (2026)  Potential structure-immunostimulatory activity relationship of Tartary buckwheat sprout pectic polysaccharides: Influences of molecular mass and esterification degree.  FOOD RESEARCH INTERNATIONAL,      [PMID:] [10.1016/j.foodres.2026.118949]
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