CYCLAMIC ACID

US Previously Marketed

First approved in 1950

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H13NO3S
Molecular Weight	179.237
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(=O)(=O)NC1CCCCC1

InChI

InChIKey=HCAJEUSONLESMK-UHFFFAOYSA-N

InChI=1S/C6H13NO3S/c8-11(9,10)7-6-4-2-1-3-5-6/h6-7H,1-5H2,(H,8,9,10)

HIDE SMILES / InChI

Molecular Formula	C6H13NO3S
Molecular Weight	179.237
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.fda.gov/downloads/food/ingredientspackaginglabeling/foodadditivesingredients/ucm404344.pdf
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/10653518 |https://www.ncbi.nlm.nih.gov/pubmed/22579423

Cyclamic acid (Cyclamate) is banned in the United States but it is used in many other Western countries without safety concerns. Cyclamate interacts with the sweet taste receptor subunit T1R3 transmembrane domain. Initially it was recommended for use in treatment of obese patients and by individuals with diabetes but in August 27, 1970 FDA concluded that there was no substantial evidence of effectiveness of cyclamate compounds at any level for treatment of obese patients and individuals with diabetes and therefore prohibited continued sale of cyclamate containing products with drug labeling. cyclamate is the putative carcinogenic agent. Cyclamate was tested in the Maximal Electroshock Seizure model (mice, ip), showing moderate anticonvulsant activity.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
taste 1 receptor member 3 2 Target ID: 83756.0 Gene Symbol: TAS1R3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16076846 \| https://www.ncbi.nlm.nih.gov/pubmed/25853419	Agonist 2752		3.1 mM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Obesity 206 Sources: https://www.fda.gov/downloads/food/ingredientspackaginglabeling/foodadditivesingredients/ucm404344.pdf	Primary	Approved 8583	Sucaryl Approved Use Unknown Launch Date 1952
Diabetes mellitus 93 Sources: https://www.fda.gov/downloads/food/ingredientspackaginglabeling/foodadditivesingredients/ucm404344.pdf	Primary	Approved 8583	Sucaryl Approved Use Unknown Launch Date 1952
Seizures 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22579423	Primary	Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
400 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379387/	2.2 g 3 times / day steady-state, oral dose: 2.2 g route of administration: Oral experiment type: STEADY-STATE co-administered:		CYCLOHEXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
1912 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379387/	2.2 g 3 times / day steady-state, oral dose: 2.2 g route of administration: Oral experiment type: STEADY-STATE co-administered:		CYCLOHEXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1379387/	2.2 g 3 times / day steady-state, oral dose: 2.2 g route of administration: Oral experiment type: STEADY-STATE co-administered:		CYCLOHEXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY500018	https://www.001chemical.com/chem/100-88-9
3B Scientific (Wuhan) Corp	3B3-024122	http://www.3bsc.com/index/pro_info.php?id=45199
AA Blocks	AA000050	https://www.aablocks.com/goods/Goods/detail?id=AA000050
Aaron Chemicals	AR0000WS	http://www.aaronchem.com/100-88-9
abcr GmbH	AB140447	http://www.abcr.com/shop/en/AB140447
AbMole Bioscience	M2543	http://www.abmole.com/products/cyclamic-acid.html
Achemica	ACMC-2097t2	http://www.achemica.com/prodinfo/?id=118512
Adooq BioScience	A12756	https://www.adooq.com/cyclamic-acid.html
AHH Chemical co.,ltd	MT-07066	http://www.ahhchemical.com/product/MT-07066.html
AHH Chemical co.,ltd	MT-07067	http://www.ahhchemical.com/product/MT-07067.html
AK Scientific, Inc. (AKSCI)	7545AF	http://www.aksci.com/item_detail.php?cat=7545AF
Alichem	490008776	http://www.alichem.com/en/products/100-88-9.html
Angel Pharmatech	AG121560	http://www.angelpharmatech.com/100-88-9.html
Anward	ANW-14388	http://www.anward.com/pro_result/26988
ApexBio Technology	B1921	http://www.apexbt.com/cyclamic-acid.html
Aurora Fine Chemicals LLC	A17.878.604	http://online.aurorafinechemicals.com/info?ID=A17.878.604
BioSynth	J-000244	https://www.biosynth.com/en/products/all-products/products/J-000244.html
BLD Pharm	BD122721	http://www.bldpharm.com/products/100-88-9.html
BOC Sciences	1215770-73-2	https://isotope.bocsci.com/product/cyclamic-acid-d11-cas-1215770-73-2-347321.html
Chem Scene	CS-2641	http://www.chemscene.com/100-88-9.html
ChemFish Tokyo co.,ltd	7533	http://www.chemfish.co.jp/index.php?id=4862&project=product
ChemMol	49417352	http://www.chemmol.com/chemmol/49417352.html
ChemMol	49426719	http://www.chemmol.com/chemmol/49426719.html
Chemspace	CSSB00000058671	https://chem-space.com/CSSB00000058671
Clearsynth	CS-T-51404	https://www.clearsynth.com/en/CST51404.html
CSNpharm	CSN10718	https://www.csnpharm.com/products/cyclamic-acid.html
eNovation Chemicals	D950732	https://www.enovationchem.com/ProductDetails.asp?ProductID=D950732
Finetech	FT-0624197	http://www.finetechnology-ind.com/prod/detail/pub/100-88-9.html
FondChemical	FDB-3184	http://www.fondchemical.com/cpshow_cid_8_pid_2459.html
iChemical	EBD43040	http://www.ichemical.com/chemicals/cas-100-88-9
Lab Network	LN00198139	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00198139
LGC Standards	DRE-C11816990	https://www.lgcstandards.com/US/en/p/DRE-C11816990
LGC Standards	MM0678.05	https://www.lgcstandards.com/US/en/p/MM0678.05
mcule	MCULE-4630986316	https://mcule.com/MCULE-4630986316/
MedChem Express	HY-B0541	https://www.medchemexpress.com/cyclamic-acid.html
Molcore	MC500018	https://www.molcore.com/product/100-88-9
MuseChem	I000102	https://www.musechem.com/product/I000102.html
Parchem	37613	https://www.parchem.com/chemical-supplier-distributor/Cyclamic-acid-037613.aspx
Sigma-Aldrich	1152600_USP	https://www.sigmaaldrich.com/catalog/product/usp/1152600?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	29550_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/29550?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S772711	https://www.smolecule.com/products/s772711
TCI (Tokyo Chemical Industry)	C0486	http://www.tcichemicals.com/eshop/en/us/commodity/C0486/index.html
THE BioTek	bt-253016	https://www.thebiotek.com/product/inhibitors/bt-253016
Vitas-M Laboratory	STL356798	http://www.request.vitasmlab.com/index.php?option=com_search_stk&Itemid=22&stk=STL356798&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink

PubMed

Title	Date	PubMed
Effects of artificial sweeteners on body weight, food and drink intake.	2010-12	21138816
[Simultaneous determination of six synthetic sweeteners in food by high performance liquid chromatography-tandem mass spectrometry].	2010-11	21381416
Retention behaviour of some high-intensity sweeteners on different SPE sorbents.	2010-10-15	20875571
Novel monocyclam derivatives as HIV entry inhibitors: Design, synthesis, anti-HIV evaluation, and their interaction with the CXCR4 co-receptor.	2010-08-02	20533501
Sensory quality of functional beverages: bitterness perception and bitter masking of olive leaf extract fortified fruit smoothies.	2010-08-01	20722953
[Determination of five synthetic sweeteners in wines using high performance liquid chromatography-tandem mass spectrometry].	2010-08	21261041
Chronic consumption of fructose rich soft drinks alters tissue lipids of rats.	2010-06-23	20573247
Gain weight by "going diet?" Artificial sweeteners and the neurobiology of sugar cravings: Neuroscience 2010.	2010-06	20589192
Performance of conventional multi-barrier drinking water treatment plants for the removal of four artificial sweeteners.	2010-06	20462625
Responses of single chorda tympani taste fibers of the calf (Bos taurus).	2010-06	20212013
Key amino acid residues involved in multi-point binding interactions between brazzein, a sweet protein, and the T1R2-T1R3 human sweet receptor.	2010-05-14	20302879
Positive allosteric modulators of the human sweet taste receptor enhance sweet taste.	2010-03-09	20173092
Tailored adsorption of His6-tagged protein onto nickel(II)-cyclam grafted mesoporous silica.	2010-02-21	20126734
Oxovanadium(IV) cyclam and bicyclam complexes: potential CXCR4 receptor antagonists.	2010-02-01	20039648
An attempt to use sweeteners as a material for accident dosimetry.	2010-02	20065713
Anionic leak currents through the Na+/monocarboxylate cotransporter SMCT1.	2010-01	19864324
Evaluation of certain food additives. Seventy-first report of the Joint FAO/WHO Expert Committee on Food Additives.	2010	20942228
Sugar alcohols, caries incidence, and remineralization of caries lesions: a literature review.	2010	20339492
Genetic and molecular basis of individual differences in human umami taste perception.	2009-08-21	19696921
A phase II study on safety and efficacy of high-dose N-acetylcysteine in patients with cystic fibrosis.	2009-08-12	19666395
Analysis and occurrence of seven artificial sweeteners in German waste water and surface water and in soil aquifer treatment (SAT).	2009-07	19533103
Development and single-laboratory validation of an HPLC method for the determination of cyclamate sweetener in foodstuffs.	2009-05	19680936
Determination of nine intense sweeteners in foodstuffs by high-performance liquid chromatography and evaporative light-scattering detection: interlaboratory study.	2009-04-23	19382579
Simultaneous determination of nonnutritive sweeteners in foods by HPLC/ESI-MS.	2009-04-22	19275236
Magnetic behaviour of nickel-cyclam complexes in mesoporous silica: EPR investigations.	2009-02-18	21817350
Sweet taste receptor expressed in pancreatic beta-cells activates the calcium and cyclic AMP signaling systems and stimulates insulin secretion.	2009	19352508
Zolpidem, a clinical hypnotic that affects electronic transfer, alters synaptic activity through potential GABA receptors in the nervous system without significant free radical generation.	2008-12-19	20046645
The capsaicin receptor participates in artificial sweetener aversion.	2008-11-28	18804451
Determination of cyclamate in foods by ultraperformance liquid chromatography/tandem mass spectrometry.	2008-11-05	18980124
Spanish Ketogenic Mediterranean Diet: a healthy cardiovascular diet for weight loss.	2008-10-26	18950537
Simultaneous square-wave voltammetric determination of aspartame and cyclamate using a boron-doped diamond electrode.	2008-07-30	18585340
Catalyzed oxidative corrosion of porous silicon used as an optical transducer for ligand-receptor interactions.	2008-07-21	18576449
[Compound preservative and cyclamat determinated by gas chromatography].	2008-07	18839542
Direct NMR detection of the binding of functional ligands to the human sweet receptor, a heterodimeric family 3 GPCR.	2008-06-11	18481853
Estimated intake of intense sweeteners from non-alcoholic beverages in Denmark, 2005.	2008-06	18484294
Chemical carcinogenesis studies in nonhuman primates.	2008	18941297
The binding site for neohesperidin dihydrochalcone at the human sweet taste receptor.	2007-10-12	17935609
Influence of artificial sweetener on human blood glucose concentration.	2007-10-05	17982603
Influence of artificial sweeteners on the kinetic and metabolic behavior of Lactobacillus delbrueckii subsp. bulgaricus.	2007-10	17969628
Synthesis, characterization and antimycobacterial activity of Ag(I)-aspartame, Ag(I)-saccharin and Ag(I)-cyclamate complexes.	2007-10	17912678
Molecular mechanism of action of monocyclam versus bicyclam non-peptide antagonists in the CXCR4 chemokine receptor.	2007-09-14	17599916
Life-span exposure to low doses of aspartame beginning during prenatal life increases cancer effects in rats.	2007-09	17805418
Artificial sweeteners and salts producing a metallic taste sensation activate TRPV1 receptors.	2007-08	17567713
Simultaneous determination of nine intense sweeteners in foodstuffs by high performance liquid chromatography and evaporative light scattering detection--development and single-laboratory validation.	2007-07-20	17540386
Rapid determination of cyclamate in foods by solid-phase extraction and capillary electrophoresis.	2007-06-22	17433340
[Restless legs due to ingestion of 'light' beverages containing saccharine. Results of an N-of-1 trial].	2007-06	17695214
Structures of artificial sweeteners--cyclamic acid and sodium cyclamate with other cyclamates.	2007-06	17507755
A conductive pathway generated from fragments of the human red cell anion exchanger AE1.	2007-05-15	17317744
Estimated intake of intense sweeteners from non-alcoholic beverages in Denmark.	2007-03	17364923
[Optimization of preparative technique for banxia-houpu effervescent tablets by orthogonal design].	2006-10	17326411

Patents

Sample Use Guides

In Vivo Use Guide

5 mg cyclamate/kg bodyweight/day or less

Route of Administration: Oral

In Vitro Use Guide

The addition of sodium cyclamate (75 mM) to the culture of the native bacterial population of the caecum concurrent with the progressive dilution of the growth medium promoted metabolism of cyclamate to cyclohexylamine (sulphamatase activity) within 4 wk. The maximum formation of cyclohexylamine was attained in about 8 wk and was equivalent to a 2-3% molar conversion of cyclamate to cyclohexylamine.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:55:27 GMT 2025` Edited by `admin` on `Mon Mar 31 17:55:27 GMT 2025`
Record UNII	HN3OFO5036
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

NSC-220327

Preferred Name

English

CYCLAMIC ACID

Official Name

English

Cyclamic acid [WHO-DD]

Common Name

English

CYCLAMIC ACID [MART.]

Common Name

English

CYCLAMATE

Common Name

English

Cyclohexanesulfamic acid

Systematic Name

English

E-952(I)

Code

English

CYCLAMIC ACID [USAN]

Common Name

English

CYCLAMIC ACID [II]

Common Name

English

INS-952(I)

Code

English

CYCLAMIC ACID [MI]

Common Name

English

CYCLAMIC ACID [USP-RS]

Common Name

English

INS NO.952(I)

Code

English

CYCLAMIC ACID [HSDB]

Common Name

English

HEXAMIC ACID

Brand Name

English

Classification Tree Code System Code

CFR

21 CFR 189.135