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Cas Database

131986-45-3

131986-45-3

Identification

  • Product Name:Pyridine,3-[4-(hexyloxy)-1,2,5-thiadiazol-3-yl]-1,2,5,6-tetrahydro-1-methyl-

  • CAS Number: 131986-45-3

  • EINECS:

  • Molecular Weight:281.422

  • Molecular Formula: C14H23N3OS

  • HS Code:2934999090

  • Mol File:131986-45-3.mol

Synonyms:5-(4-Hexyloxy-[1,2,5]thiadiazol-3-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine;

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Safety information and MSDS view more

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowed

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:3-(Hexyloxy)-4-(1-Methyl-1,2,5,6-Tetrahydropyridin-3-Yl)-1,2,5-Thiadiazole
  • Packaging:25mg
  • Price:$ 220
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Xanomeline L-tartrate hydrate ≥98% (HPLC)
  • Packaging:5mg
  • Price:$ 199
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Xanomeline L-tartrate hydrate ≥98% (HPLC)
  • Packaging:25mg
  • Price:$ 854
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:3-(Hexyloxy)-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1,2,5-thiadiazole 95+%
  • Packaging:1g
  • Price:$ 1485
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:3-(Hexyloxy)-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1,2,5-thiadiazole 95+%
  • Packaging:500mg
  • Price:$ 1073
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:3-(Hexyloxy)-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1,2,5-thiadiazole 95+%
  • Packaging:250mg
  • Price:$ 695
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:Xanomeline 95+%
  • Packaging:250mg
  • Price:$ 405
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:Xanomeline 95+%
  • Packaging:1g
  • Price:$ 1010
  • Delivery:In stock
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  • Manufacture/Brand:Chemenu
  • Product Description:3-(Hexyloxy)-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1,2,5-thiadiazole 95%
  • Packaging:1g
  • Price:$ 711
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  • Manufacture/Brand:Arctom
  • Product Description:Xanomeline ≥95%
  • Packaging:5mg
  • Price:$ 69
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Relevant articles and documentsAll total 7 Articles be found

Tacrine-xanomeline and tacrine-iperoxo hybrid ligands: Synthesis and biological evaluation at acetylcholinesterase and M1 muscarinic acetylcholine receptors

Cirillo, Davide,Dallanoce, Clelia,De Amici, Marco,Holzgrabe, Ulrike,Maspero, Marco,Messerer, Regina,Sotriffer, Christoph,Volpato, Daniela,Yuan Chen, Natalia

, (2020/02/11)

We synthesized a set of new hybrid derivatives (7-C8, 7-C10, 7-C12 and 8-C8, 8-C10, 8-C12), in which a polymethylene spacer chain of variable length connected the pharmacophoric moiety of xanomeline, an M1/M4-preferring orthosteric muscarinic agonist, with that of tacrine, a well-known acetylcholinesterase (AChE) inhibitor able to allosterically modulate muscarinic acetylcholine receptors (mAChRs). When tested in vitro in a colorimetric assay for their ability to inhibit AChE, the new compounds showed higher or similar potency compared to that of tacrine. Docking analyses were performed on the most potent inhibitors in the series (8-C8, 8-C10, 8-C12) to rationalize their experimental inhibitory power against AChE. Next, we evaluated the signaling cascade at M1 mAChRs by exploring the interaction of Gαq-PLC-β3 proteins through split luciferase assays and the myo-Inositol 1 phosphate (IP1) accumulation in cells. The results were compared with those obtained on the known derivatives 6-C7 and 6-C10, two quite potent AChE inhibitors in which tacrine is linked to iperoxo, an exceptionally potent muscarinic orthosteric activator. Interestingly, we found that 6-C7 and 6-C10 behaved as partial agonists of the M1 mAChR, at variance with hybrids 7-Cn and 8-Cn containing xanomeline as the orthosteric molecular fragment, which were all unable to activate the receptor subtype response.

Towards the development of new subtype-specific muscarinic receptor radiopharmaceuticals - Radiosynthesis and ex vivo biodistribution of [ 18F]3-(4-(2-(2-(2-fluoroethoxy)ethoxy)ethylthio)-1,2, 5-thiadiazol-3-yl)-1-methyl-1,2,5,6-tetrahydropyrid

Van Oosten, Erik M.,Wilson, Alan A.,Mamo, David C.,Pollock, Bruce G.,Mulsant, Benoit H.,Houle, Sylvain,Vasdev, Neil

experimental part, p. 1222 - 1232 (2011/02/24)

Muscarinic receptors have been implicated in neurological disorders including Alzheimer's disease, Parkinson's disease, and schizophrenia. Nineteen derivatives of thiadiazolyltetrahydropyridine (TZTP), a core that has previously shown high affinities towa

Synthesis and evaluation of xanomeline analogs-Probing the wash-resistant phenomenon at the M1 muscarinic acetylcholine receptor

Kane, Brian E.,Grant, Marianne K.O.,El-Fakahany, Esam E.,Ferguson, David M.

, p. 1376 - 1392 (2008/09/18)

A series of xanomeline analogs were synthesized and evaluated for binding at the M1 muscarinic acetylcholine receptor (M1 receptor). Specifically, compounds that substitute the O-hexyl chain of xanomeline with polar, ionizable, or conformationally restricted moieties were assessed for their ability to bind to the M1 receptor in a wash-resistant manner (persistent binding). From our screen, several novel ligands that persistently bind to the M1 receptor with greater affinity than xanomeline were discovered. Results indicate that persistent binding may arise not only from hydrophobic interactions but also from ionic interactions with a secondary M1 receptor binding site. Herein, a qualitative model that accounts for both binding scenarios is proposed and applied to understand the structural basis to wash-resistant binding and long-acting effects of xanomeline-based compounds.

Combination therapy for treatment of psychoses

-

, (2008/06/13)

The invention provides combination therapy comprising a first component which is a typical antipsychotic or an atypical antipsychotic and a second component which is a muscarinic agonist for the treatment of psychoses and other disorders.

Method for treating anxiety

-

, (2008/06/13)

The present invention provides a method for treating anxiety in humans using of Formula I herein disclosed compounds.

Process route upstream and downstream products

Process route

3-(3-Pentyloxy-1,2,5-thiadiazol-4-yl)-1-methylpyridinium iodide
131988-16-4

3-(3-Pentyloxy-1,2,5-thiadiazol-4-yl)-1-methylpyridinium iodide

xanomeline
131986-45-3

xanomeline

Conditions
Conditions Yield
With methanol; sodium tetrahydroborate; at 20 ℃;
75%
3-(4-hexyloxy-1,2,5-thiadiazol-3-yl)-1-methylpyridinium iodide
131988-19-7

3-(4-hexyloxy-1,2,5-thiadiazol-3-yl)-1-methylpyridinium iodide

xanomeline
131986-45-3

xanomeline

Conditions
Conditions Yield
With sodium tetrahydroborate; In ethanol; at -10 ℃; for 1h;
With sodium tetrahydroborate; In ethanol;
With sodium tetrahydroborate; In ethanol; for 3h; Heating;
3-(3-Chloro-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine
131986-59-9

3-(3-Chloro-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine

hexan-1-ol
111-27-3

hexan-1-ol

xanomeline
131986-45-3

xanomeline

Conditions
Conditions Yield
hexan-1-ol; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;
3-(3-Chloro-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine; In tetrahydrofuran; Reflux;
60%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

xanomeline
131986-45-3

xanomeline

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: acetic acid / water / 23 h / 0 - 20 °C
2.1: ammonium chloride; ammonium hydroxide / water / 22 h / 20 °C
3.1: disulfur dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C
4.1: sodium hydride / tetrahydrofuran / 2 h / 0 - 20 °C
4.2: 3 h / Reflux
5.1: acetone / 20 °C
6.1: sodium tetrahydroborate; methanol / 20 °C
With methanol; disulfur dichloride; ammonium hydroxide; sodium tetrahydroborate; sodium hydride; ammonium chloride; acetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone;
2-hydroxy-2-(pyridin-3-yl)acetonitrile
17604-74-9,107986-64-1

2-hydroxy-2-(pyridin-3-yl)acetonitrile

xanomeline
131986-45-3

xanomeline

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: ammonium chloride; ammonium hydroxide / water / 22 h / 20 °C
2.1: disulfur dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C
3.1: sodium hydride / tetrahydrofuran / 2 h / 0 - 20 °C
3.2: 3 h / Reflux
4.1: acetone / 20 °C
5.1: sodium tetrahydroborate; methanol / 20 °C
With methanol; disulfur dichloride; ammonium hydroxide; sodium tetrahydroborate; sodium hydride; ammonium chloride; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone;
2-amino-2-(pyridin-3-yl)acetonitrile
131988-63-1

2-amino-2-(pyridin-3-yl)acetonitrile

xanomeline
131986-45-3

xanomeline

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: disulfur dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C
2.1: sodium hydride / tetrahydrofuran / 2 h / 0 - 20 °C
2.2: 3 h / Reflux
3.1: acetone / 20 °C
4.1: sodium tetrahydroborate; methanol / 20 °C
With methanol; disulfur dichloride; sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;
3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine
131986-28-2

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine

xanomeline
131986-45-3

xanomeline

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: sodium hydride / tetrahydrofuran / 2 h / 0 - 20 °C
1.2: 3 h / Reflux
2.1: acetone / 20 °C
3.1: sodium tetrahydroborate; methanol / 20 °C
With methanol; sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; acetone;
3-(4-hexyloxy-1,2,5-thiadiazol-3-yl)pyridine
131987-69-4

3-(4-hexyloxy-1,2,5-thiadiazol-3-yl)pyridine

xanomeline
131986-45-3

xanomeline

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: acetone / 20 °C
2: sodium tetrahydroborate; methanol / 20 °C
With methanol; sodium tetrahydroborate; In acetone;
xanomeline
131986-45-3

xanomeline

Conditions
Conditions Yield

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