Varacin

Varacin  Varacin skeletal structure

Names
Preferred IUPAC name

2-(8,9-Dimethoxy-1,2,3,4,5-benzopentathiepin-6-yl)ethan-1-amine

Identifiers

CAS Number

* 134029-48-4 Y

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL151233 N

ChemSpider |

* 156044 N

PubChem CID

* 179269

CompTox Dashboard (EPA)

* DTXSID10158465

InChI

* InChI=1S/C10H13NO2S5/c1-12-7-5-6(3-4-11)9-10(8(7)13-2)15-17-18-16-14-9/h5H,3-4,11H2,1-2H3 N

Key: HIKCOAGMCNIBMP-UHFFFAOYSA-N N

* InChI=1/C10H13NO2S5/c1-12-7-5-6(3-4-11)9-10(8(7)13-2)15-17-18-16-14-9/h5H,3-4,11H2,1-2H3

Key: HIKCOAGMCNIBMP-UHFFFAOYAP

SMILES

* NCCc2cc(OC)c(OC)c1SSSSSc12

Properties

Chemical formula

| C10H13NO2S5
Molar mass | 339.540 g/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)

Infobox references

Chemical compound

Varacin is a bicyclic organosulfur compound originally found in marine Ascidiacea from the Polycitor genus.[1] It contains an unusual pentathiepin ring which reacts with DNA, and varacin and synthetic analogues have been investigated for their antimicrobial and antitumour properties.[2][3] Because of its potent biological activity and unusual and challenging ring system, it has been a popular target of efforts toward its total synthesis.[4][5][6]

By virtue of the unsymmetrically substituted benzopentathiepin ring system, varacin and a few related polysulfane natural products exist as potentially isolable enantiomers as a result of planar chirality.[7]

## References

[edit]

1. ^ Makarieva TN, Stonik VA, Dmitrenok AS, Grebnev BB, Isakov VV, Rebachyk NM, Rashkes YW (February 1995). "Varacin and three new marine antimicrobial polysulfides from the far-eastern ascidian Polycitor sp". Journal of Natural Products. 58 (2): 254–8\. doi:10.1021/np50116a015. PMID 7769392.
2. ^ Greer A (October 2001). "On the origin of cytotoxicity of the natural product varacin. A novel example of a pentathiepin reaction that provides evidence for a triatomic sulfur intermediate". Journal of the American Chemical Society. 123 (42): 10379–86\. doi:10.1021/ja016495p. PMID 11603989.
3. ^ Brzostowska EM, Greer A (January 2003). "The role of amine in the mechanism of pentathiepin (polysulfur) antitumor agents". Journal of the American Chemical Society. 125 (2): 396–404\. doi:10.1021/ja027416s. PMID 12517151.
4. ^ Behar V, Danishefsky SJ (1993-07-01). "Total synthesis of the novel benzopentathiepin varacinium trifluoroacetate: the viability of "varacin-free base"". Journal of the American Chemical Society. 115 (15): 7017–7018\. doi:10.1021/ja00068a087. ISSN 0002-7863.
5. ^ Ford PW, Narbut MR, Belli J, Davidson BS (1994-10-01). "Synthesis and Structural Properties of the Benzopentathiepins Varacin and Isolissoclinotoxin A". The Journal of Organic Chemistry. 59 (20): 5955–5960\. doi:10.1021/jo00099a026. ISSN 0022-3263.
6. ^ Toste FD, Still IW (1995-07-01). "A New Route to the Synthesis of the Naturally Occurring Benzopentathiepin Varacin". Journal of the American Chemical Society. 117 (27): 7261–7262\. doi:10.1021/ja00132a033.
7. ^ Brzostowska, Edyta M.; Paulynice, Martine; Bentley, Ronald; Greer, Alexander (2007-07-01). "Planar Chirality due to a Polysulfur Ring in Natural Pentathiepin Cytotoxins. Implications of Planar Chirality for Enantiospecific Biosynthesis and Toxicity". Chemical Research in Toxicology. 20 (7): 1046–1052\. doi:10.1021/tx7000465. ISSN 0893-228X.

* v
* t
* e

Phenethylamines

Phenethylamines|

* Psychedelics: 3,4-DMPEA-NDEPA
* 25B-NBOMe
* 25C-NBOMe
* 25D-NBOMe
* 25D-NM-NDEAOP
* 25H-NBOMe
* 25I-NBOMe
* 25N-NBOMe
* 25O-NBOMe
* 2C-B
* 2C-B-AN
* 2C-Bn
* 2C-Bu
* 2C-C
* 2C-CN
* 2C-CP
* 2C-D
* 2C-E
* 2C-EF
* 2C-F
* 2C-G
* 2C-G-2
* 2C-G-3
* 2C-G-4
* 2C-G-5
* 2C-G-6
* 2C-G-N
* 2C-H
* 2C-I
* 2C-iBu
* 2C-iP
* 2C-N
* 2C-NH2
* 2C-O
* 2C-O-2
* 2C-O-4
* 2C-P
* 2C-Ph
* 2C-SE
* 2C-T
* 2C-T-2
* 2C-T-3
* 2C-T-4
* 2C-T-5
* 2C-T-6
* 2C-T-7
* 2C-T-8
* 2C-T-9
* 2C-T-10
* 2C-T-11
* 2C-T-12
* 2C-T-13
* 2C-T-14
* 2C-T-15
* 2C-T-16
* 2C-T-17
* 2C-T-18
* 2C-T-19
* 2C-T-20
* 2C-T-21
* 2C-T-22
* 2C-T-22.5
* 2C-T-23
* 2C-T-24
* 2C-T-25
* 2C-T-27
* 2C-T-28
* 2C-T-30
* 2C-T-31
* 2C-T-32
* 2C-T-33
* 2C-tBu
* 2C-TFE
* 2C-TFM
* 2C-YN
* 2C-V
* Allylescaline
* CT-5172
* DESOXY
* Escaline
* Isoproscaline
* M-NDEPA
* Macromerine
* MEPEA
* Mescaline
* Metaescaline
* Methallylescaline
* N-DEAOP-NMPEA
* N-Methylmescaline
* Proscaline
* Psi-2C-T-4

* Stimulants: Phenylethanolamine
* Hordenine
* Phenethylamine
* Phenpromethamine
* α-Methylphenethylamine (amphetamine)
* β-Methylphenethylamine
* m-Methylphenethylamine
* N-Methylphenethylamine
* o-Methylphenethylamine
* p-Methylphenethylamine
* Phenacylamine (β-ketophenethylamine)
* Solriamfetol

* Entactogens: Lophophine
* MDPEA
* MDMPEA

* Others: Amidephrine
* ASR-2001
* Biscaline
* BOH
* Buscaline
* Denopamine
* Desvenlafaxine
* DMPEA
* F-17475
* Phenibut
* Pronethalol
* Salbutamol
* Levosalbutamol
* Trichocereine
* Venlafaxine

Amphetamines|

* Psychedelics: 3C-AL
* 3C-BZ
* 3C-E
* 3C-MAL
* 3C-P
* Aleph
* Beatrice
* Bromo-DragonFLY
* D-Deprenyl
* DMA
* DMMDA
* DOB
* DOB-NDEPA
* DOC
* DOEF
* DOET
* DOI
* DOI-NDEPA
* DOM
* DOM-NDEPA
* DON
* DOPR
* DOTFM
* DOTFM-NDEPA
* Ganesha
* MMDA
* MMDA-2
* Psi-DOM
* TMA
* TMA-2
* TMA-2-NDEPA
* TeMA
* ZDCM-04

* Stimulants: 2-FA
* 2-FMA
* 3-FA
* 3-FMA
* β-Phenylmethamphetamine
* Acridorex
* Alfetamine
* Amfecloral
* Amfepentorex
* Amphetamine
* Dextroamphetamine
* Levoamphetamine
* Amphetaminil
* Benfluorex
* Benzphetamine
* Cathine
* Clobenzorex
* Dimethylamphetamine
* Ephedrine
* Ephenidine
* Etafedrine
* Etilamfetamine
* Famprofazone
* Fencamfamin
* Fencamine
* Fenethylline
* Fenfluramine
* Dexfenfluramine
* Levofenfluramine
* Fenproporex
* Flucetorex
* Fludorex
* Formetorex
* Furfenorex
* Gepefrine
* 4-Hydroxyamphetamine
* Iofetamine
* Isopropylamphetamine
* Lefetamine
* Lisdexamfetamine
* Mefenorex
* Metaraminol
* Methamphetamine
* Dextromethamphetamine
* Levomethamphetamine
* Methoxamine
* Methoxyphenamine
* MMA
* Morforex
* Norfenfluramine
* L-Norpseudoephedrine
* α,N-Diethylphenylethylamine
* Oxifentorex
* Oxilofrine
* Ortetamine
* PBA
* PBMA
* PCA
* PCMA
* PFA
* PFMA
* PIA
* PIMA
* PMA
* PMEA
* PMMA
* Phenylpropanolamine
* Pholedrine
* Prenylamine
* Propylamphetamine
* Pseudoephedrine
* Sibutramine
* Tiflorex
* Xylopropamine
* Zylofuramine

* Entactogens: 4-FA
* 4-FMA
* 4-MA
* 4-MMA
* 4-MTA
* 5-APB
* 5-APDB
* 5-EAPB
* 5-IT
* 5-MAPB
* 5-MAPDB
* 6-APB
* 6-APDB
* 6-Chloro-MDMA
* 6-EAPB
* 6-IT
* 6-MAPB
* 6-MAPDB
* EDA
* IAP
* 2,3-MDA
* 3,4-MDA (tenamfetamine)
* MDEA
* MDHMA
* MDMA (midomafetamine)
* MDOH
* Methamnetamine
* MMDMA
* Naphthylaminopropane
* TAP

* Others: 3,4-DCA
* Amiflamine
* Cafedrine
* Deprenyl
* D-Deprenyl
* Selegiline (L-deprenyl)
* DiFMDA
* Thiamphenicol
* UWA-101 (α-cPr-MDMA)

Phentermines|

* Stimulants: Chlorphentermine
* Cloforex
* Clortermine
* Etolorex
* Mephentermine
* Pentorex
* Phentermine

* Entactogens: MDPH
* MDMPH

* Others: Cericlamine

Cathinones|

* Stimulants: 3-FMC
* 4-MC
* 4-BMC
* 4-CMC
* 4-EMC
* 4-FMC
* 4-MEC
* 4-MeMABP
* 4-MPD
* Amfepramone
* Benzedrone
* Brephedrone
* Buphedrone
* Bupropion
* Cathinone
* Dimethylcathinone
* Ethcathinone
* Eutylone
* Hydroxybupropion
* Methcathinone
* Methedrone
* NEB
* N-Ethylhexedrone
* N-Ethylpentedrone
* Pentedrone
* Pentylone

* Entactogens: 3,4-DMMC
* 3-MMC
* Butylone
* Ethylone
* Methylone
* Methylenedioxycathinone
* Mephedrone
* Propylone

Phenylisobutylamines
(and further-extended)|

* Entactogens: 4-CAB
* 4-MAB
* Ariadne
* BDB
* Butylone
* EBDB
* Eutylone
* MBDB

* Stimulants: α-Propylphenethylamine
* Hexapradol
* Phenylisobutylamine (α-ethylphenethylamine)

Catecholamines
(and close relatives)|

* 6-FNE
* 6-OHDA
* α-Me-DA
* α-Me-TRA
* Adrenochrome
* Arbutamine
* Ciladopa
* D-DOPA (dextrodopa)
* Dimetofrine
* Dobutamine
* Dopamine
* Dopexamine
* Epinephrine (adrenaline)
* Epinine
* Etilefrine
* Ethylnorepinephrine
* Fenclonine
* Ibopamine
* Isoprenaline
* Isoetarine
* L-DOPA (levodopa)
* L-DOPS (droxidopa)
* L-Phenylalanine
* L-Tyrosine
* m-Tyramine
* Metanephrine
* Metaraminol
* Metaterol
* Metirosine
* Methyldopa
* N,N-Dimethyldopamine
* Nordefrin
* Levonordefrin
* Norepinephrine (noradrenaline)
* Norfenefrine (m-octopamine)
* Normetanephrine
* Orciprenaline
* p-Octopamine
* p-Tyramine
* Phenylephrine
* Synephrine
* Theodrenaline

Cyclized
phenethylamines|

| Phenylalkylpyrrolidines|

* α-PBP
* α-PHP
* α-PPP
* α-PVP
* MDPBP
* MDPPP
* MDPV
* 4-MePBP
* 4-MePHP
* 4-MePPP
* Fluorolintane
* MOPPP
* MOPVP
* MPBP
* MPHP
* MPPP
* Naphyrone
* PEP
* Prolintane
* Pyrovalerone

|

2-Benzylpiperidines
(phenidates)|

* 2-Benzylpiperidine
* 3-Bromomethylphenidate
* 3-Chloromethylphenidate
* 3-Methylmethylphenidate
* 3,4-Dichloro-2-benzylpiperidine
* 3,4-Dichloroethylphenidate
* 3,4-Dichloromethylphenidate
* 4-Bromoethylphenidate
* 4-Bromomethylphenidate
* 4-Chloromethylphenidate
* 4-Fluoroethylphenidate
* 4-Fluoroisopropylphenidate
* 4-Fluoromethylphenidate
* 4-Methyl-2-benzylpiperidine
* 4-Methylisopropylphenidate
* 4-Methylmethylphenidate
* 4-Nitromethylphenidate
* α-Acetyl-2-benzylpiperidine
* α-Keto-2-benzylpiperidine
* CPMBP
* Desoxypipradrol (2-DPMP)
* Difemetorex
* Ethylnaphthidate (HDEP-28)
* Ethylphenidate
* Isopropylnaphthidate
* Isopropylphenidate
* MDMPH
* Methylnaphthidate (HDMP-28)
* Methylphenidate
* Phacetoperane
* Pipradrol
* Propylphenidate
* Rimiterol
* Ritalinamide
* Ritalinic acid
* SCH-5472
* Serdexmethylphenidate

Phenylmorpholines
(phenmetrazines)|

* (2R,3R)-Hydroxybupropion
* 2-(2,5-Dimethoxy-4-bromophenyl)morpholine
* 2-Fluorophenmetrazine
* 2-Methylphenmetrazine
* 2-Phenylmorpholine
* 2-Phenyl-3,6-dimethylmorpholine
* 3-Chlorophenmetrazine (PAL-594)
* 3-Fluorophenetrazine
* 3-Fluorophenmetrazine (PAL-593)
* 3-Methoxyphenmetrazine
* 3-Methylphenmetrazine (PAL-773)
* 4-Fluorophenmetrazine (PAL-748)
* 4-Methylphendimetrazine
* 4-Methylphenmetrazine (PAL-747)
* 2C-B-morpholine
* Fenbutrazate
* Fenmetramide
* Flumexadol
* G-130
* Isophenmetrazine
* Manifaxine
* Methylenedioxyphenmetrazine
* Morazone
* N-Ethylphenmetrazol
* Naphthylmetrazine (PAL-704)
* Naphthylmorpholine (PAL-678)
* Oxaflozane
* PDM-35
* PF-219,061)
* Phendimetrazine
* Phenetrazine
* Phenmetetrazine
* Phenmetrazine
* Phenmetrazol
* Pseudophenmetrazine
* Radafaxine ((2S,3S)-hydroxybupropion)

Phenyloxazolamines
(aminorexes)|

* 3-Methylaminorex
* 4-Ethylaminorex (4-EAR)
* 4'-Fluoroaminorex
* 4-Methylaminorex (4-MAR)
* 4,4'-Dimethylaminorex (4,4'-DMAR)
* 2C-B-aminorex
* 2F-MAR
* 4B-MAR
* 4C-MAR
* 4F-MAR
* Aminorex
* Clominorex
* Cyclazodone
* Ephedroxane
* Fenozolone
* Fluminorex
* MDMAR
* Methylenedioxyaminorex (MDAR)
* N-Methylcyclazodone
* N,N-Dimethylaminorex
* Pemoline
* Thozalinone

Isoquinolines and
tetrahydroisoquinolines|

* Anhalamine
* Anhalidine
* Anhalinine
* Anhalonidine
* Anhalonine
* Anhalotine
* Arizonine
* Calycotomine
* Carnegine (pectenine)
* Corypalline
* Debrisoquine
* Deglucopterocereine
* Deutetrabenazine
* Diclofensine
* DOB-CR
* DOM-CR
* Esproquin
* Gigantine
* Hedycarine
* Heliamine
* Hydrastinine
* Hydrocotarnine
* Hydrohydrastinine (MDMTHIQ; MDMA-CR)
* Isoanhalamine
* Isoanhalidine
* Isoanhalonidine
* Isocorypalline
* Isopellotine
* Isosalsoline
* Lemaireocereine
* Longimammamine
* Longimammatine
* Longimammidine
* Longimammosine
* Lophocerine
* Lophophorine
* Lophotine
* MDMA-CR
* Mescalotam
* N-Methylanhalinine
* N-Methylheliamine
* N-Methylisosalsoline
* N-Methyl-DOM-CR (Beatrice-CR)
* N-Methyl-THIQ (METH-CR)
* Nomifensine
* Norsalsolinol
* Nortehaunine
* Norweberine
* O-Methylanhalonidine
* O-Methylpellotine
* Pachycereine
* Pellotine
* Perafensine
* Peyoglutam
* Peyophorine
* Peyotine
* PMMA-CR
* Quinisocaine
* Reticuline
* Salsolidine
* Salsoline
* Salsolinol
* TDIQ (MDTHIQ, MDA-CR)
* Tehaunine
* Tehaunine N-oxide
* Tepenine
* Tetrabenazine
* Tetrahydroisoquinoline (THIQ; AMPH-CR)
* Tetrahydropapaveroline
* Tilisolol
* Tretoquinol
* Uberine
* Valbenazine
* Weberidine
* Weberine
* Zelandopam

2-Aminoindanes|

* 2-Aminoindane (2-AI)
* 5-IAI
* Aprindine
* BFAI
* BFMAI
* DHAI
* DOM-AI
* ETAI
* Indanorex
* Indantadol
* MDAI
* MDMAI
* MEAI (5-MeO-AI)
* MMAI
* NM-2-AI
* PNU-99,194
* TAI

2-Aminotetralins|

* 2-Aminotetralin (2-AT)
* 5-OH-DPAT
* 6-CAT
* 7-OH-DPAT
* 8-OH-DPAT
* AS-19
* CHF-1024
* DOM-AT
* MDAT
* MDMAT
* Nolomirole
* UH-232

Others / unsorted|

* 1-Aminomethylindanes (e.g., 2CB-Ind, AMMI, bromojimscaline, jimscaline)
* 2-ADN
* 2-Benzhydrylpyrrolidine
* 2C-B-5-hemiFLY-α6 (BNAP)
* 2C-B-PYR
* 2CBecca
* 2CJP
* 2CLisaB
* 2CLisaH
* 3-Benzhydrylmorpholine
* 3-Phenylpiperidines (e.g., 3-phenylpiperidine, 3-PPP, OSU-6162 (PNU-96391), LPH-5, LPH-48, Z3517967757 (Z7757))
* 6-AB
* AL-1095
* Aminochromes (e.g., adrenochrome, adrenolutin)
* Benzazepines (e.g., fenoldopam, lorcaserin, SCHEMBL5334361)
* Benzocyclobutenes (e.g., 2CBCB-NBOMe, bromotomscaline, S33005, TCB-2, tomscaline)
* Benzoxepins (e.g., BBOX, IBOX, TFMBOX)
* Butyltolylquinuclidine
* Camfetamine
* Cypenamine (trans-2-phenylcyclopentylamine)
* Diphenidine
* Diphenylprolinol
* DMBMPP
* Ergolines (e.g., LSD)
* Fencamfamin
* GYKI-52895
* HDMP-29
* Ivabradine
* Methoxphenidine
* Methylmorphenate
* Milnacipran
* MT-45
* 2-Naphthylamine
* Org 6582
* Partial ergolines (e.g., NDTDI, RU-27849, DEIMDHPCA, DEMPDHPCA, DEMPDHPCA-2C-D, RU-27251)
* PF-592,379
* Phenylcyclopropylamines (e.g., DMCPA, TMT, tranylcypromine)
* Phenylpiracetams (e.g., phenylpiracetam, MRZ-9547, RGPU-95)
* Pyridopyrroloquinoxalines (e.g., lumateperone, deulumateperone, IHCH-7079, IHCH-7086, IHCH-7113, ITI-1549)
* Tetrahydrobenzopyranylamines (e.g., CT-5126)
* Tolazoline
* Tricyclics (e.g., AMDA, AMDH, benzoctamine, dizocilpine, SpAMDA)
* ZC-B

Related compounds|

* 2-Furylethylamine
* 2-Pyrrolylethylamine
* 3-Pyrrolylethylamine
* 3-Pyrrolylpropylamine
* 2-Tetrahydrofurylethylamine
* 4-Benzylpiperidine
* 7-AB
* Alkylamines (e.g., 1,3-DMBATooltip 1,3-dimethylbutylamine, 1,4-DMAATooltip 1,4-dimethylamylamine, heptaminol, iproheptine, isometheptene, methylhexanamine/1,3-DMAA, octodrine, oenethyl, tuaminoheptane)
* Benzylamines (e.g., benzylamine, α-methylbenzylamine, MDM1EA, ALPHA, M-ALPHA, pargyline)
* Benzylpiperazines (e.g., benzylpiperazine, MDBZP, fipexide)
* Cyclohexylaminopropanes (e.g., propylhexedrine, norpropylhexedrine)
* Cyclopentylaminopropanes (e.g., isocyclamine, cyclopentamine)
* Phenoxyethylamines (e.g., 3,4,5-trimethoxyphenoxyethylamine, CT-4719, ORG-37684)
* Phenylalkenylamines (e.g., phenylbutenamine)
* Phenylalkynylamines (e.g., phenylbutynamine)
* Phenylpiperazines (e.g., 1-phenylpiperazine, mCPPTooltip meta-chlorophenylpiperazine, TFMPPTooltip trifluoromethylphenylpiperazine, oMPPTooltip ortho-methylphenylpiperazine, pFPPTooltip para-fluorophenylpiperazine, pMeOPPTooltip para-methoxyphenylpiperazine)
* Phenylpropylamines (e.g., phenylpropylamine, homo-MDA, homo-MDMA)
* Thienylaminopropanes (thiopropamines) (e.g., thiopropamine, methiopropamine, thiothinone)

* See also: Tryptamines
* Ergolines and lysergamides
* Stimulants
* Entactogens
* Psychedelics

This article about a heterocyclic compound is a stub. You can help Wikipedia by expanding it.

|

* v
* t
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*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[1,3-DMBA]: 1,3-dimethylbutylamine
*[1,4-DMAA]: 1,4-dimethylamylamine
*[1,3-DMAA]: 1,3-dimethylamylamine
*[mCPP]: meta-chlorophenylpiperazine
*[TFMPP]: trifluoromethylphenylpiperazine
*[oMPP]: ortho-methylphenylpiperazine
*[pFPP]: para-fluorophenylpiperazine
*[pMeOPP]: para-methoxyphenylpiperazine