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1. Calcium Cyclamate
2. Cyclamate
3. Cyclamate Calcium (2:1) Salt
4. Cyclamate, Calcium
5. Cyclamate, Calcium (2:1) Salt, Dihydrate
6. Cyclamate, Potassium
7. Cyclamate, Sodium
8. Cyclamate, Sodium Salt
9. Cyclamates
10. Potassium Cyclamate
11. Sodium Cyclamate
1. Cyclohexylsulfamic Acid
2. 100-88-9
3. Cyclamate
4. Cyclohexanesulfamic Acid
5. N-cyclohexylsulfamic Acid
6. Hexamic Acid
7. Sucaryl
8. Sucaryl Acid
9. Cyclohexylaminesulphonic Acid
10. N-cyclohexylsulphamic Acid
11. Sulfamic Acid, Cyclohexyl-
12. Polycat 200
13. Cyclohexylamidosulfuric Acid
14. Cyclohexylaminesulfonic Acid
15. Cylamic Acid
16. Cyclohexylsulphamic Acid
17. Cyclohexanesulphamic Acid
18. Zyklamat
19. Cyclohexylamidosulphuric Acid
20. Cyclohexylamide Sulfate
21. Cyclohexylamine Sulfamic Acid
22. Sulfamic Acid, N-cyclohexyl-
23. Nsc 220327
24. Hexamic Acid (tn)
25. Nsc-220327
26. Cyclamate, Sodium Salt
27. Hn3ofo5036
28. Cyclohexylsulfamic Acid;cyclamate
29. Ins No.952(i)
30. Chebi:15964
31. Ins-952(i)
32. Asugryn
33. Nsc220327
34. Ncgc00165999-01
35. Cyclamic Acid (usan)
36. E-952(i)
37. Dsstox_cid_21809
38. Dsstox_rid_79849
39. Dsstox_gsid_41809
40. Cyclamic Acid [usan]
41. Cyclamates
42. Cyclamsaeure
43. Cyclamate, Calcium
44. Cyclamic Acid [usan:ban]
45. Cas-100-88-9
46. C6h13no3s
47. Cyclamate, Potassium
48. Hsdb 275
49. N-cyclohexylsulfamsaeure
50. Einecs 202-898-1
51. Sulfuric Acid Monoamide, N-cyclohexyl-
52. Brn 2208885
53. Unii-hn3ofo5036
54. Cyclamic-acid
55. N-(cyclohexyl)aminosulfonsaeure
56. Sucaryl Acidxine
57. Cyclamic Acid
58. Cyclamate Calcium (2:1) Salt
59. (cyclamic Acid)
60. Calciumlevulinate
61. Cyclohexylamide Sulphate
62. Cyclohexyl-sulfamic Acid
63. Cyclamic Acid-[d11]
64. N-cyclohexyl-sulfamic Acid
65. Bmse000657
66. N-?cyclohexylsulfamic Acid
67. N-cyclo-hexylsulphamic Acid
68. Cyclamic Acid [ii]
69. Cyclamic Acid [mi]
70. Schembl6227
71. Cyclamic Acid, Ban, Usan
72. Cyclamic Acid [hsdb]
73. 4-12-00-00102 (beilstein Handbook Reference)
74. Cyclamic Acid [mart.]
75. Cyclohexansulfamidsa Currencyure
76. Cyclohexylamine-n-sulfonic Acid
77. Cyclamic Acid [usp-rs]
78. Cyclamic Acid [who-dd]
79. Chembl1206440
80. Dtxsid5041809
81. Hms3264k03
82. Hms3652c17
83. Pharmakon1600-01301015
84. Hy-b0541
85. Zinc1529532
86. N-cyclohexyl-sulfuric Acid Monoamide
87. Tox21_112285
88. Tox21_301008
89. Mfcd00065234
90. Nsc760133
91. S4015
92. Stl356798
93. Akos015913947
94. Tox21_112285_1
95. Ccg-213726
96. Nsc-760133
97. Ncgc00165999-02
98. Ncgc00165999-03
99. Ncgc00254910-01
100. As-59382
101. N-cyclohexylsulfamic Acid, >=98.0% (t)
102. Ft-0624197
103. Sw219574-1
104. C02824
105. D02442
106. E78799
107. Ab01563182_01
108. Ab01563182_02
109. Sr-01000940120
110. J-000244
111. Q2130929
112. Sr-01000940120-2
113. Cyclamic Acid, United States Pharmacopeia (usp) Reference Standard
| Molecular Weight | 179.24 g/mol |
|---|---|
| Molecular Formula | C6H13NO3S |
| XLogP3 | 0.6 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 2 |
| Exact Mass | 179.06161445 g/mol |
| Monoisotopic Mass | 179.06161445 g/mol |
| Topological Polar Surface Area | 74.8 Ų |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Complexity | 200 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
2. 2= SLIGHTLY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) IS 5-15 G/KG, BETWEEN 1 PINT & 1 QUART FOR 70 KG PERSON (150 LB). /NA SALT/
Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-243
Sweetening Agents
Substances that sweeten food, beverages, medications, etc., such as sugar, saccharine or other low-calorie synthetic products. (From Random House Unabridged Dictionary, 2d ed) (See all compounds classified as Sweetening Agents.)
In pregnant rats, significant amounts of sodium cyclamate were distributed to fetal tissues. /Sodium cyclamate/
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 201 (1999)
Absorption of cyclamate from the gut is incomplete, and absorbed cyclamate is excreted in the urine. When three men received 1 g calcium (14)C-cyclamate orally, 87-90% was recovered in the urine and feces in about equal amounts within four days. /Calcium cyclamate/
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 201 (1999)
When given to lactating dogs and rats, calcium cyclamate reached higher concentrations in the milk than in the blood. /Calcium cyclamate/
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 201 (1999)
In guinea-pigs, rats and rabbits, 30, 50 and 5% of orally administered cyclamate was excreted in the feces and 65, 40 and 95% in the urine, respectively, over two to three days. Cyclamate thus appears to be readily absorbed by rabbits but less readily by guinea-pigs and rats.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 201 (1999)
For more Absorption, Distribution and Excretion (Complete) data for CYCLAMATE (11 total), please visit the HSDB record page.
Most humans convert only small amounts of cyclamate to cyclohexylamine, and the majority converted < 0.1-8%; however, there is wide interindividual variation in the daily urinary excretion of cyclohexylamine, which can amount to 60% of a dose of cyclamate. Gastrointestinal microflora are the source of the conversion of unabsorbed cyclamate to cyclohexylamine.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 201 (1999)
Orally administered cyclamate appears to be readily absorbed by rabbits but less readily by guinea-pigs, rats and humans. All of these species convert cyclamate to cyclohexylamine, via the action of gastrointestinal microflora on unabsorbed cyclamate. The metabolism of cyclohexylamine to other products differs somewhat in humans and other species, although most cyclohexylamine is rapidly excreted unchanged in the urine. In rats, it is metabolized mainly by hydroxylation of the cyclohexane ring; in humans, it is metabolized by deamination; and in guinea-pigs and rabbits, it is metabolized by ring hydroxylation and deamination.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 202 (1999)
Two metabolites were definitely identified in the urine of volunteers who received an oral dose of (14)C-cyclohexylamine, namely cyclohexanol and trans-cyclohexane-1,2- diol. No N-hydroxycyclohexylamine was found in human urine.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 201 (1999)
...TO DETERMINE INDUCTION OF CYCLOHEXYLAMINE PRODUCTION...2 GROUPS OF RATS WERE FED NORMAL DIETS WITH & WITHOUT CYCLAMATE FOR 8 MO. BOTH GROUPS...WERE THEN GIVEN (14)C-CYCLAMATE...THOSE FED FORMER DIET CONVERTED 18% OF (14)C-DOSE INTO CYCLOHEXYLAMINE...THOSE FED LATTER CONVERTED LESS THAN 1%. ...DIETARY PRETREATMENT WITH CYCLAMATE IS USUALLY NECESSARY BEFORE.../BIOTRANSFORMATION/ TO CYCLOHEXYLAMINE...IN MAN, RAT, GUINEA-PIG, & RABBIT.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 149
For more Metabolism/Metabolites (Complete) data for CYCLAMATE (9 total), please visit the HSDB record page.
(14)C-labelled cyclamate was shown to have an average serum half-life of 8 hours in dogs and rats.
WHO/FAO: Expert Committee on Food Additives. FAO Nutrition Meetings Report Series No. 48A: Calcium Cyclamate and Sodium Cyclamate (Including Cyclohexylamine) (1970). Available from, as of July 13, 2011: https://www.inchem.org/pages/jecfa.html
The sweet taste receptor is a heterodimer of two G protein coupled receptors, T1R2 and T1R3. Previous experimental studies using sweet receptor chimeras and mutants show that there are at least three potential binding sites in this heterodimeric receptor. Receptor activity toward the artificial sweeteners aspartame and neotame depends on residues in the amino terminal domain of human T1R2. In contrast, receptor activity toward the sweetener cyclamate and the sweet taste inhibitor lactisole depends on residues within the transmembrane domain of human T1R3. Furthermore, receptor activity toward the sweet protein brazzein depends on the cysteine rich domain of human T1R3.
PMID:17168764 Cui M, et al; Curr Pharm Des 12 (35): 4591-4600 (2006)
The sweet protein brazzein [recombinant protein with sequence identical with the native protein lacking the N-terminal pyroglutamate (the numbering system used has Asp2 as the N-terminal residue)] activates the human sweet receptor, a heterodimeric G-protein-coupled receptor composed of subunits Taste type 1 Receptor 2 (T1R2) and Taste type 1 Receptor 3 (T1R3). In order to elucidate the key amino acid(s) responsible for this interaction, we mutated residues in brazzein and each of the two subunits of the receptor. The effects of brazzein mutations were assayed by a human taste panel and by an in vitro assay involving receptor subunits expressed recombinantly in human embryonic kidney cells; the effects of the receptor mutations were assayed by in vitro assay. We mutated surface residues of brazzein at three putative interaction sites: site 1 (Loop43), site 2 (N- and C-termini and adjacent Glu36, Loop33), and site 3 (Loop9-19). Basic residues in site 1 and acidic residues in site 2 were essential for positive responses from each assay. Mutation of Y39A (site 1) greatly reduced positive responses. A bulky side chain at position 54 (site 2), rather than a side chain with hydrogen-bonding potential, was required for positive responses, as was the presence of the native disulfide bond in Loop9-19 (site 3). Results from mutagenesis and chimeras of the receptor indicated that brazzein interacts with both T1R2 and T1R3 and that the Venus flytrap module of T1R2 is important for brazzein agonism. With one exception, all mutations of receptor residues at putative interaction sites predicted by wedge models failed to yield the expected decrease in brazzein response. The exception, hT1R2 (human T1R2 subunit of the sweet receptor):R217A/hT1R3 (human T1R3 subunit of the sweet receptor), which contained a substitution in lobe 2 at the interface between the two subunits, exhibited a small selective decrease in brazzein activity. However, because the mutation was found to increase the positive cooperativity of binding by multiple ligands proposed to bind both T1R subunits (brazzein, monellin, and sucralose) but not those that bind to a single subunit (neotame and cyclamate), we suggest that this site is involved in subunit-subunit interaction rather than in direct brazzein binding. Results from this study support a multi-point interaction between brazzein and the sweet receptor by some mechanism other than the proposed wedge models.
PMID:20302879 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2879441 Assadi-Porter FM, et al; J Mol Biol 398 (4): 584-94 (2010)
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