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(S)-2-METHYL-4-BENZYLPIPERAZINE, with the molecular formula C13H18N2, is a piperazine derivative characterized by the presence of a methyl and a benzyl group attached to the nitrogen atom. It is widely recognized in the fields of pharmacology and medicinal chemistry for its role as a building block in the synthesis of pharmaceutical drugs and biologically active molecules.

132871-12-6

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132871-12-6 Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-2-METHYL-4-BENZYLPIPERAZINE is used as a key intermediate in the synthesis of various pharmaceutical drugs and biologically active molecules. Its unique structure allows for the creation of compounds with potential therapeutic properties.
Used in Therapeutic Applications:
In the medical field, (S)-2-METHYL-4-BENZYLPIPERAZINE is used as a potential treatment for conditions such as anxiety, depression, and neurological disorders. Its pharmacological properties are being studied for their ability to address these health issues effectively.
Used as a Drug Delivery Vehicle:
(S)-2-METHYL-4-BENZYLPIPERAZINE has been investigated for its potential as a drug delivery vehicle. Its structure may facilitate the targeted delivery of therapeutic agents, improving the efficacy and reducing the side effects of treatments.
Used as a Targeting Ligand in Drug Design:
Furthermore, (S)-2-METHYL-4-BENZYLPIPERAZINE is utilized as a targeting ligand in drug design. This application takes advantage of its ability to bind specifically to certain biological targets, thereby enhancing the selectivity of drug action and potentially leading to more effective therapies.
Overall, (S)-2-METHYL-4-BENZYLPIPERAZINE is a versatile compound that plays a crucial role in the development of new pharmaceutical compounds and drug delivery systems, offering promising avenues for improving patient care and treatment outcomes.

Check Digit Verification of cas no

The CAS Registry Mumber 132871-12-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,2,8,7 and 1 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 132871-12:
(8*1)+(7*3)+(6*2)+(5*8)+(4*7)+(3*1)+(2*1)+(1*2)=116
116 % 10 = 6
So 132871-12-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H18N2/c1-11-9-14(8-7-13-11)10-12-5-3-2-4-6-12/h2-6,11,13H,7-10H2,1H3/t11-/m0/s1

132871-12-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name (3S)-1-benzyl-3-methylpiperazine

1.2 Other means of identification

Product number -
Other names AB3085

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:132871-12-6 SDS

132871-12-6Relevant articles and documents

Structure-Activity Relationship Studies on Oxazolo[3,4- a]pyrazine Derivatives Leading to the Discovery of a Novel Neuropeptide S Receptor Antagonist with Potent in Vivo Activity

Albanese, Valentina,Ruzza, Chiara,Marzola, Erika,Bernardi, Tatiana,Fabbri, Martina,Fantinati, Anna,Trapella, Claudio,Reinscheid, Rainer K.,Ferrari, Federica,Sturaro, Chiara,Calò, Girolamo,Amendola, Giorgio,Cosconati, Sandro,Pacifico, Salvatore,Guerrini, Remo,Preti, Delia

, p. 4089 - 4108 (2021/04/12)

Neuropeptide S modulates important neurobiological functions including locomotion, anxiety, and drug abuse through interaction with its G protein-coupled receptor known as neuropeptide S receptor (NPSR). NPSR antagonists are potentially useful for the treatment of substance abuse disorders against which there is an urgent need for new effective therapeutic approaches. Potent NPSR antagonists in vitro have been discovered which, however, require further optimization of their in vivo pharmacological profile. This work describes a new series of NPSR antagonists of the oxazolo[3,4-a]pyrazine class. The guanidine derivative 16 exhibited nanomolar activity in vitro and 5-fold improved potency in vivo compared to SHA-68, a reference pharmacological tool in this field. Compound 16 can be considered a new tool for research studies on the translational potential of the NPSergic system. An in-depth molecular modeling investigation was also performed to gain new insights into the observed structure-activity relationships and provide an updated model of ligand/NPSR interactions.

Efficient one-pot synthesis of enantiomerically pure: N -protected-α-substituted piperazines from readily available α-amino acids

Jida, Mouhamad,Ballet, Steven

, p. 1595 - 1599 (2018/02/09)

A new pathway towards enantiomerically pure 3-substituted piperazines, bearing a benzyl protecting group, has been developed in good overall yields (83-92%), starting from commercially available N-protected amino acids. The methodology represents an efficient and simple one-pot procedure, employing a synthetic sequence consisting of an Ugi-4 component reaction, a Boc-deprotection, an intramolecular cyclisation reaction and a final reduction (UDCR). From the benzyl protected precursors, the 2-substituted piperazines bearing a Boc-protecting group could consequently also be obtained via a simple protection and deprotection step of the corresponding piperazines. The practical utility of this methodology was demonstrated for chiral drug synthesis.

Enantiomerically pure piperazines via NaBH4/I2reduction of cyclic amides

Harish, Vagala,Periasamy, Mariappan

, p. 175 - 180 (2017/01/11)

Enantiomerically pure (3S,7R,8aS)-3-phenyloctahydropyrrolo[1,2-a]pyrazine-7-ol, (3S,7R,8aS)-3-methyl octahydropyrrolo[1,2-a]pyrazine-7-ol, (3S,7R,8aS)-3-isopropyloctahydropyrrolo[1,2-a]pyrazine-7-ol and (3S,7R,8aS)-3-isobutyloctahydropyrrolo[1,2-a]pyrazine-7-ol 16d were synthesized via preparation of the corresponding cyclic amides from enantiomerically pure L-proline and hydroxyproline derivatives followed by reduction using sodium borohydride-iodine.

Synthesis and structure of 1,4-dipiperazino benzenes: Chiral terphenyl-type peptide helix mimetics

Maity, Prantik,Koenig, Burkhard

supporting information; experimental part, p. 1473 - 1476 (2009/04/10)

(Chemical Equation Presented) The terphenyl structure has been proven to be an ideal scaffold mimicking side-chain functionalities of peptidic α-helices. The synthesis of 1,4-dipiperazino benzenes, using stepwise transition metal-catalyzed N-arylation of chiral piperazines to a central benzene core is reported. The structure determination by X-ray crystallography reveals a geometrical arrangement of the hydrophobic side chains resembling the orientation of key i, i + 3, and i + 7 positions in a peptidic α-helix or in terphenyl helix mimetics.

PIPERAZINE UREA DERIVATIVES AS MELANOCORTIN-4 RECEPTOR AGONISTS

-

Page 80, (2010/11/30)

Certain novel piperazine urea derivatives are agonists of the human melanocortin-4 receptor (MC-4R) and, in particular, are receptor-subtype selective agonists of MC-4R. They are useful for the treatment, control, or prevention of diseases and disorders r

A novel and facile method to synthesize (R)- and (S)-2-methylpiperazine

Liu, Bo,Xu, Guang-Yu,Yang, Chun-Hao,Wu, Xi-Han,Xie, Yu-Yuan

, p. 4111 - 4118 (2007/10/03)

A concise and efficient synthesis of (R)- and (S)-2-methylpiperazine in only five steps from (D)- and (L)-alanine is described. The key step is reaction of benzylamine with a bifunctional molecule to build a six-membered ring.

Anti-inflammatory piperazinyl-benzyl-tetrazole derivatives and intermediates thereof

-

, (2008/06/13)

This invention relates to tetrazoles and their pharmaceutically acceptable salts which are selective agonists for the delta opioid receptor, particularly useful in the treatment of inflammatory diseases such as arthritis, psoriasis, asthma, inflammatory bowel disease, disorders or respiratory function, gastrointestinal disorders such as functional bowel disease and functional GI disorders, of formula (I) wherein R1is H, C2-C6alkanoyl, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, (C3-C7cycloalkyl)-(C1-C4alkyl), (C1-C4alkoxy)-(C1-C4alkyl), carboxy-(C1-C4alkyl), aryl-(C1-C4alkyl) or heteroaryl-(C1-C4alkyl); R2and R3are each independently H or C1-C4alkyl; R4is selected from (i) H, (ii) a group of the formula R6—(CH2)m—Z—(CH2)n—, where m is 0, 1, 2 or 3, n is 1, 2 or 3, Z is a direct link or O, and R6is —CO2H or —CO2(C1-C4alkyl), and (iii) a group of formula (a) where R7is H or C1-C4alkyl; and R5is hydroxy, C1-C4alkoxy or —NHSO2(C1-C4alkyl); with the proviso that when Z is O, m is 1, 2 or 3 and n is 2 or 3.

Exploring the structure-activity relationships of [1-(4-(4- tert-butyl-3'-hydroxy)benzhydryl-4-benzylpiperazine] (SL-3111), a high-affinity and selective δ-opioid receptor nonpeptide agonist ligand

Alfaro-Lopez, Josue,Okayama, Toru,Hosohata, Keiko,Davis, Peg,Porreca, Frank,Yamamura, Henry I.,Hruby, Victor J.

, p. 5359 - 5368 (2007/10/03)

SL-3111 [1-(4-tert-butyl-3'-hydroxy)benzhydryl-4- benzylpiperazine] is a de novo designed, high-affinity and selective nonpeptide peptidomimetic agonist of the δ-opioid receptor. In a previous report we had described the unique biological characteristics of this ligand and also a need for further structural evaluation. To pursue this, we have introduced a completely different heterocyclic template (2 and 3), which, based on molecular modeling studies, may present the required structural features to properly orient the pharmacophore groups. We also have made more subtle changes to the original piperazine scaffold (5 and 11). The biological activities of these compounds revealed an important participation of the scaffold in the ligand-receptor interaction. To further explore functional diversity on the scaffold, we have maintained the original piperazine ring and introduced four different functionalities at position 2 of the heterocyclic ring (15a-d; a = CH2-O-CH2-Ph; b = Me; c = CH2Ph; d = CH2OH). The biological activities observed for these compounds showed a very interesting trend in terms of the steric effects of the groups introduced at this position. A decrease of almost 2000-fold in affinity and potency at the δ- receptor was observed for 15c compared with 15b. This difference may be explained if we postulate that the bioactive conformation of these peptidomimetics is close to the minimal energy conformations calculated in our study. On the basis of these findings we have realized the importance of this position to further explore and simplify the structure of future generations of peptidomimetic ligands.

Asymmetric Synthesis of 2,6-Methylated Piperazines

Mickelson, John W.,Belonga, Kenneth L.,Jacobsen, Jon E.

, p. 4177 - 4183 (2007/10/02)

The complete series of enantiopure 2,6-methylated piperazines was synthesized utilizing two alternative reactions in the key bond-forming step.The dimethyl enantiomers, (2R,6R)- and (2S,6S)-2,6-dimethylpiperazine (1, 2), were prepared using either a diastereoselective triflate alkylation or a novel intermolecular Mitsunobu reaction to set the required stereochemistry.The monomethyl derivatives, (R)- and (S)-tert-butyl 2-methyl-1-piperazinecarboxylate (3, 4) were also synthesized employing the Mitsunobu cyclization strategy while the trimethyl compounds, (R)- and (S)-2,2,6- trimethylpiperazine (5, 6) were prepared using an enantiospecific triflate alkylation as the principal reaction.These methods represent efficient, general strategies for preparing a variety of 2,6-methylated piperazines for which the absolute stereochemistry can be readily controlled.

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